Hydrochloric Acid → 6-{2-(2-Chloro-phenyl)-5-[4-(Pyrimidin-2-yloxy)-phenyl]-pyrrol-1-ylmethyl}-pyridin-2-ylamine hydrochloride
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([CH2:26][C:27]2[N:32]=[C:31]([NH2:33])[CH:30]=[CH:29][CH:28]=2)[C:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]3[N:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[CH:15][CH:14]=2)=[CH:11][CH:12]=1.Cl>C(OCC)C>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([CH2:26][C:27]2[N:32]=[C:31]([NH2:33])[CH:30]=[CH:29][CH:28]=2)[C:10]([C:13]2[CH:14]=[CH:15][C:16]([O:19][C:20]3[N:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[CH:17][CH:18]=2)=[CH:11][CH:12]=1Participants
4
Procedure
To a solution of 6-{2-(2-chlorophenyl)-5-[4-(pyrimidin-2-yloxy)-phenyl]pyrrol-1-ylmethyl}pyridin-2-ylamine (0.032 g, 0.070 mmol) in diethyl ether (1 mL) was added a 2.0 M solution of HCl (0.035 mL, 0.070 mmol) in diethyl ether and the mixture stirred at room temperature for 30 min. The suspension was then concentrated and the resulting solid triturated with hexanes to afford the title compound (0.032 g, 86%) as an off-white solid: Rf0.38 (97.5:2.5 methylene chloride/methanol); mp 135-140° C.; 1H NMR (300 MHz, CD3OD) δ 8.60 (d, J=4.8 Hz, 2H), 7.50-7.00 (m, 10H), 6.65 (d, J=8.7 Hz, 1H), 6.44 (d, J=3.6 Hz, 1H), 6.36 (d, J=3.6 Hz, 1H), 5.86 (d, J=8.7 Hz, 1H), 5.16 (s, 2H); IR (ATR) 3303, 3086, 2714, 1662, 1628, 1567, 1484, 1401, 1300, 1211, 902, 855, 757 cm−1; ESI MS m/z 454 [C26H20ClN5O+H]+; HPLC (Method 1) 95.7% (AUC), tR=12.48 min. Anal. Calcd for C26H20ClN5O.HCl.1.25H2O: C, 60.88; H, 4.62; N, 13.65. Found: C, 61.12; H, 4.54; N, 13.31.