(2,3-dichlorophenyl)methanamine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: The title compound was prepared using the procedure described in Example 222B using 2,3-dichlorobenzylamine and 2-(5-isoquinolinyl)propanoic acid instead of 4-(trifluoromethoxy)benzylamine and 5-isoquinolinylacetic acid. MS (ESI+) m/z 359 (M+H)+; MS (ESI−) m/z 357 (M−H)−; 1H NMR (DMSO, 300 MHz) δ 1.54 (d, J 7.1, 3H), 4.20 (m, 2H), 4.53 (q, J 7.1, 1H), 7.17 (d, J 7.8, 1H), 7.26 (t, J 7.8, 1H), 7.52 (d, J 8.1, 1H), 7.78 (t, J 7.8, 1H), 7.91 (d, J 6.5, 1H), 8.16 (d, J 8.1, 1H), 8.24 (d, J 6.4, 1H), 8.59 (d, J 6.2, 1H), 8.66 (t, J 5.8, 1H), 9.50 (s, 1H).

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

Procedure: To a solution of triphosgene (89 mg, 0.3 mmol) in THF were added a solution of 2,3-dichlorobenzylamine (100 mg, 0.59 mmol) in THF dropwise and then DIEA (209 μL, 1.2 mmol). The reaction mixture was stirred at rt for 10 min, and 2-(methylamino)ethanol (90 mg, 1.2 mmol) was added. The reaction mixture was stirred at rt for 15 min and purified on RP-HPLC using a mixture of acetonitrile and H2O to give 3-(2,3-dichlorobenzyl)-1-(2-hydroxyethyl)-1-methylurea (70 mg, 44%). LRMS (M+H+) m/z 277.1. The reaction mixture was stirred at rt for 15 min purified on RP-HPLC a mixture of acetonitrile and H2O

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

Procedure: To a solution of triphosgene (89 mg, 0.3 mmol) in THF were added a solution of 2,3-dichlorobenzylamine (100 mg, 0.59 mmol) in THF dropwise and then DIEA (209 μL, 1.2 mmol). The reaction mixture was stirred at rt for 10 min, and 2-(methylamino)ethanol (90 mg, 1.2 mmol) was added. The reaction mixture was stirred at rt for 15 min and purified on RP-HPLC using a mixture of acetonitrile and H2O to give 3-(2,3-dichlorobenzyl)-1-(2-hydroxyethyl)-1-methylurea (70 mg, 44%). LRMS (M+H+) m/z 277.1. The reaction mixture was stirred at rt for 15 min purified on RP-HPLC a mixture of acetonitrile and H2O

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

Procedure: The title compound was prepared using the procedure described in Example 222B using 2,3-dichlorobenzylamine and 2-(5-isoquinolinyl)propanoic acid instead of 4-(trifluoromethoxy)benzylamine and 5-isoquinolinylacetic acid. MS (ESI+) m/z 359 (M+H)+; MS (ESI−) m/z 357 (M−H)−; 1H NMR (DMSO, 300 MHz) δ 1.54 (d, J 7.1, 3H), 4.20 (m, 2H), 4.53 (q, J 7.1, 1H), 7.17 (d, J 7.8, 1H), 7.26 (t, J 7.8, 1H), 7.52 (d, J 8.1, 1H), 7.78 (t, J 7.8, 1H), 7.91 (d, J 6.5, 1H), 8.16 (d, J 8.1, 1H), 8.24 (d, J 6.4, 1H), 8.59 (d, J 6.2, 1H), 8.66 (t, J 5.8, 1H), 9.50 (s, 1H).

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 0.5 gram (0.0028 mole) of 2,3-dichlorobenzylamine and 0.27 gram (0.0081 mole) of 2-chloroethylisothiocyanate in 10 mL of 1,4-dioxane was placed in a sealed reaction vial. The reaction mixture was heated to 80° C. where it stirred for about 18 hours. The reaction mixture was allowed to cool and a solid precipitate that had formed was collected by filtration. The solid was rinsed with diethyl ether and was dried under reduced pressure to yield 0.68 gram of the title compound. The NMR spectrum was consistent with the proposed structure. was placed in a sealed reaction vial to cool a solid precipitate that had formed was collected by filtration The solid was rinsed with diethyl ether was dried under reduced pressure

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 0.5 gram (0.0028 mole) of 2,3-dichlorobenzylamine and 0.27 gram (0.0081 mole) of 2-chloroethylisothiocyanate in 10 mL of 1,4-dioxane was placed in a sealed reaction vial. The reaction mixture was heated to 80° C. where it stirred for about 18 hours. The reaction mixture was allowed to cool and a solid precipitate that had formed was collected by filtration. The solid was rinsed with diethyl ether and was dried under reduced pressure to yield 0.68 gram of the title compound. The NMR spectrum was consistent with the proposed structure. was placed in a sealed reaction vial to cool a solid precipitate that had formed was collected by filtration The solid was rinsed with diethyl ether was dried under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir: