4-[2-(4-methylpiperazin-1-yl)ethoxy]benzaldehyde

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

Procedure: In a similar fashion to Compound LXXXVII, 4-(2-(4-methylpiperazin-1-yl)ethoxy)benzaldehyde (138 mg, 0.222 mmol), (1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid dimethylamide (78.7 mg, 0.244 mmol), and Ammonium acetate (34.3 mg, 0.444 mmol) were reacted to produce 34.61 mg (28%) of the title compound. (300 MHz, DMSO-d6) 12.56 (s, 1H), 8.08 (d, J=8 Hz, 1H), 7.93 (s, 1H), 7.88 (s, 1H), 7.11 (d, J=8 Hz, 1H), 6.42 (m, 2H), 6.32 (s, 1H), 5.35 (m, 1H), 4.15 (m, 2H), 3.49 (m, 1H), 3.07 (d, J=8 Hz, 1H), 3.00 (d, J=8 Hz, 1H), 2.96-2.68 (m, 14H), 2.32 (s, 2H), 2.14 (s, 2H), 1.92 (m, 1H), 1.44 (m, 1H). MS=550 (M+H), HPLC: 1.91 min. (G Method)

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

Procedure: In a similar fashion to Compound LXXXVII, 4-(2-(4-methylpiperazin-1-yl)ethoxy)benzaldehyde (138 mg, 0.222 mmol), (1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid dimethylamide (78.7 mg, 0.244 mmol), and Ammonium acetate (34.3 mg, 0.444 mmol) were reacted to produce 34.61 mg (28%) of the title compound. (300 MHz, DMSO-d6) 12.56 (s, 1H), 8.08 (d, J=8 Hz, 1H), 7.93 (s, 1H), 7.88 (s, 1H), 7.11 (d, J=8 Hz, 1H), 6.42 (m, 2H), 6.32 (s, 1H), 5.35 (m, 1H), 4.15 (m, 2H), 3.49 (m, 1H), 3.07 (d, J=8 Hz, 1H), 3.00 (d, J=8 Hz, 1H), 2.96-2.68 (m, 14H), 2.32 (s, 2H), 2.14 (s, 2H), 1.92 (m, 1H), 1.44 (m, 1H). MS=550 (M+H), HPLC: 1.91 min. (G Method)

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

Procedure: In a similar fashion to Compound LXXXVII, 4-(2-(4-methylpiperazin-1-yl)ethoxy)benzaldehyde (138 mg, 0.222 mmol), (1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid dimethylamide (78.7 mg, 0.244 mmol), and Ammonium acetate (34.3 mg, 0.444 mmol) were reacted to produce 34.61 mg (28%) of the title compound. (300 MHz, DMSO-d6) 12.56 (s, 1H), 8.08 (d, J=8 Hz, 1H), 7.93 (s, 1H), 7.88 (s, 1H), 7.11 (d, J=8 Hz, 1H), 6.42 (m, 2H), 6.32 (s, 1H), 5.35 (m, 1H), 4.15 (m, 2H), 3.49 (m, 1H), 3.07 (d, J=8 Hz, 1H), 3.00 (d, J=8 Hz, 1H), 2.96-2.68 (m, 14H), 2.32 (s, 2H), 2.14 (s, 2H), 1.92 (m, 1H), 1.44 (m, 1H). MS=550 (M+H), HPLC: 1.91 min. (G Method)