(2-prop-2-enoxyphenyl)methanamine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.0 g (16.4 mmol) of the compound from Example I are boiled under reflux for 17 hours in 250 ml of a saturated methanolic ammonia solution. The reaction mixture is evaporated in vacuo, the residue is taken up in methanol and the mixture is evaporated again; this process is repeated a few times. The crude product is taken up in dichloromethane and extracted several times with water. The aqueous phase is evaporated to a very great extent, an oil being obtained which crystallizes on standing. The reaction mixture is evaporated in vacuo the mixture is evaporated again extracted several times with water The aqueous phase is evaporated to a very great extent an oil being obtained which crystallizes on standing

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.0 g (16.4 mmol) of the compound from Example I are boiled under reflux for 17 hours in 250 ml of a saturated methanolic ammonia solution. The reaction mixture is evaporated in vacuo, the residue is taken up in methanol and the mixture is evaporated again; this process is repeated a few times. The crude product is taken up in dichloromethane and extracted several times with water. The aqueous phase is evaporated to a very great extent, an oil being obtained which crystallizes on standing. The reaction mixture is evaporated in vacuo the mixture is evaporated again extracted several times with water The aqueous phase is evaporated to a very great extent an oil being obtained which crystallizes on standing

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3 0 g (16.4 mmol) of the compound from Example I are boiled under reflux for 17 hours in 250 ml of a saturated methanolic ammonia solution. The reaction mixture is evaporated in vacuo, the residue is taken up in methanol and the mixture is evaporated again; this process is repeated a few times. The crude product is taken up in dichioromethane and extracted several times with water. The aqueous phase is evaporated to a vey great extent, an oil being obtained which crystallizes on standing. The reaction mixture is evaporated in vacuo the mixture is evaporated again extracted several times with water The aqueous phase is evaporated to a vey great extent an oil being obtained which crystallizes on standing

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3 0 g (16.4 mmol) of the compound from Example I are boiled under reflux for 17 hours in 250 ml of a saturated methanolic ammonia solution. The reaction mixture is evaporated in vacuo, the residue is taken up in methanol and the mixture is evaporated again; this process is repeated a few times. The crude product is taken up in dichioromethane and extracted several times with water. The aqueous phase is evaporated to a vey great extent, an oil being obtained which crystallizes on standing. The reaction mixture is evaporated in vacuo the mixture is evaporated again extracted several times with water The aqueous phase is evaporated to a vey great extent an oil being obtained which crystallizes on standing

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.0 g (16.4 mmol) of the compound from Example I are boiled under reflux for 17 hours in 250 ml of a saturated methanolic ammonia solution. The reaction mixture is evaporated in vacuo, the residue is taken up in methanol and the mixture is evaporated again; this process is repeated a few times. The crude product is taken up in dichloromethane and extracted several times with water. The aqueous phase is evaporated to a very great extent, an oil being obtained which crystallizes on standing. The reaction mixture is evaporated in vacuo the mixture is evaporated again extracted several times with water The aqueous phase is evaporated to a very great extent an oil being obtained which crystallizes on standing

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.0 g (16.4 mmol) of the compound from Example I are boiled under reflux for 17 hours in 250 ml of a saturated methanolic ammonia solution. The reaction mixture is evaporated in vacuo, the residue is taken up in methanol and the mixture is evaporated again; this process is repeated a few times. The crude product is taken up in dichloromethane and extracted several times with water. The aqueous phase is evaporated to a very great extent, an oil being obtained which crystallizes on standing. The reaction mixture is evaporated in vacuo the mixture is evaporated again extracted several times with water The aqueous phase is evaporated to a very great extent an oil being obtained which crystallizes on standing

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.0 g (16.4 mmol) of the compound from Example I are boiled under reflux for 17 hours in 250 ml of a saturated methanolic ammonia solution. The reaction mixture is evaporated in vacuo, the residue is taken up in methanol and the mixture is evaporated again; this process is repeated a few times. The crude product is taken up in dichloromethane and extracted several times with water. The aqueous phase is evaporated to a very great extent, an oil being obtained which crystallizes on standing. The reaction mixture is evaporated in vacuo the mixture is evaporated again extracted several times with water The aqueous phase is evaporated to a very great extent an oil being obtained which crystallizes on standing

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A yellow solution of (S)-5-(4-(but-3-en-1-yl)-4-methylpiperidin-1-yl)-6-(1-(tert-butoxy)-2-methoxy-2-oxoethyl)-7-methylimidazo[1,2-a]pyridine-2-carboxylic acid sodium salt (40 mg, 0.081 mmol, 1 equiv), 2-allyloxybenzylamine (18 mg, 0.113 mmol, 1.4 equiv), DIPEA (0.042 mL, 0.243 mmol, 3 equiv), and HATU (43 mg, 0.113 mmol, 1.4 equiv) in DMF (0.81 mL) was stirred 2 h. The reaction was then diluted with EtOAc, washed with saturated aqueous NaHCO3, dried (Na2SO4), and concentrated in vacuo. The crude product was purified by flash column chromatography (0-100% EtOAc/hex) to provide the product (30 mg, 60%) as a colorless oil. 1H NMR (400 MHz, CDCl3) [note: appears to be at least two rotamers, only major rotamer transcribed] δ 8.21 (s, 1H), 7.81 (t, J=6.1 Hz, 1H), 7.26-7.16 (m, 2H), 6.97-6.85 (m, 2H), 6.19-6.06 (m, 2H), 5.93-5.82 (m, 1H), 5.47 (dq, J=17.3, 1.5 Hz, 1H), 5.31 (dq, J=10.5, 1.4 Hz, 1H), 5.14-4.95 (m, 2H), 4.72 (d, J=6.0 Hz, 2H), 4.63 (dt, J=5.0, 1.5 Hz, 2H), 3.70 (s, 3H), 3.61-3.48 (m, 2H), 3.07 (d, J=13.8 Hz, 1H), 2.85 (d, J=12.0 Hz, 1H), 2.45 (d, J=1.0 Hz, 3H), 2.17-2.07 (m, 2H), 1.71-1.40 (m, 6H), 1.24 (s, 9H), 1.13 (s, 3H); LCMS (ESI, M+1): 617.4. washed with saturated aqueous NaHCO3 dried (Na2SO4) concentrated in vacuo The crude product was purified by flash column chromatography (0-100% EtOAc/hex)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.0 g (16.4 mmol) of the compound from Example I are boiled under reflux for 17 hours in 250 ml of a saturated methanolic ammonia solution. The reaction mixture is evaporated in vacuo, the residue is taken up in methanol and the mixture is evaporated again; this process is repeated a few times. The crude product is taken up in dichloromethane and extracted several times with water. The aqueous phase is evaporated to a very great extent, an oil being obtained which crystallizes on standing. The reaction mixture is evaporated in vacuo the mixture is evaporated again extracted several times with water The aqueous phase is evaporated to a very great extent an oil being obtained which crystallizes on standing

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.0 g (16.4 mmol) of the compound from Example I are boiled under reflux for 17 hours in 250 ml of a saturated methanolic ammonia solution. The reaction mixture is evaporated in vacuo, the residue is taken up in methanol and the mixture is evaporated again; this process is repeated a few times. The crude product is taken up in dichloromethane and extracted several times with water. The aqueous phase is evaporated to a very great extent, an oil being obtained which crystallizes on standing. The reaction mixture is evaporated in vacuo the mixture is evaporated again extracted several times with water The aqueous phase is evaporated to a very great extent an oil being obtained which crystallizes on standing

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3 0 g (16.4 mmol) of the compound from Example I are boiled under reflux for 17 hours in 250 ml of a saturated methanolic ammonia solution. The reaction mixture is evaporated in vacuo, the residue is taken up in methanol and the mixture is evaporated again; this process is repeated a few times. The crude product is taken up in dichioromethane and extracted several times with water. The aqueous phase is evaporated to a vey great extent, an oil being obtained which crystallizes on standing. The reaction mixture is evaporated in vacuo the mixture is evaporated again extracted several times with water The aqueous phase is evaporated to a vey great extent an oil being obtained which crystallizes on standing