4-(Aminomethyl)benzonitrile → N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[4-(propan-2-yl)piperazin-1-yl]-1,3-thiazole-5-carboxamide

HRID 717933Notes

Reaction equation

HRID 717933 reaction equation
C([C:3]1[CH:10]=[CH:9]C(CN)=CC=1)#N.Br[C:12]1[S:13][C:14]([C:17]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][N:24]3[CH:27]=[CH:28][N:29]=[C:23]3[CH:22]=2)=[O:18])=[CH:15][N:16]=1.BrC1SC(C(NC2C=C[C:42]3[N:43]([CH:45]=[CH:46][N:47]=3)[CH:44]=2)=O)=CN=1>>[N:29]1[CH:28]=[CH:27][N:24]2[CH:25]=[CH:26][C:21]([CH2:20][NH:19][C:17]([C:14]3[S:13][C:12]([N:47]4[CH2:42][CH2:44][N:43]([CH:10]([CH3:9])[CH3:3])[CH2:45][CH2:46]4)=[N:16][CH:15]=3)=[O:18])=[CH:22][C:23]=12

Participants

4

Reactant 3

HCID 826084-(Aminomethyl)benzonitrileHCID 867019292-bromo-N-(imidazo[1,2-a]pyridin-6-yl)thiazole-5-carboxamideHCID 867019472-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiazole-5-carboxamide

Product 1

HCID 72699524N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[4-(propan-2-yl)piperazin-1-yl]-1,3-thiazole-5-carboxamide

Procedure

The title compound was prepared as in Example 53B, substituting 1-isopropylpiperazine for 4-cyanobenzylamine and 2-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiazole-5-carboxamide for 2-bromo-N-(imidazo[1,2-a]pyridin-6-yl)thiazole-5-carboxamide. 1H NMR (300 MHz, DMSO-d6) ppm 8.80 (t, J=5.9 Hz, 1H), 8.48 (d, J=7.1 Hz, 1H), 7.88 (s, 1H), 7.87 (s, 1H), 7.52 (d, J=1.4 Hz, 1H), 7.37 (s, 1H), 6.81 (dd, J=7.1, 1.7 Hz, 1H), 4.42 (d, J=6.1 Hz, 2H), 3.41-3.48 (m, 4H), 2.64-2.79 (m, 1H), 2.51-2.57 (m, 4H), 0.98 (d, J=6.4 Hz, 6H); MS (ESI(+)) m/e 385 (M+H)+.

Sources & evidence

ORD record
ord-20db0c45698c4bc1b76fb5f584461ec0
Source dataset
uspto-grants-2015_11
Patent number
US09193723B2

Reaction notes

Loading…