2-(Trifluoromethyl)-1H-benzimidazole → 2-(1-((4-morpholino-2-(2-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)pyrido[3,2-d]pyrimidin-6-yl)methyl)piperidin-4-yl)propan-2-ol

HRID 2091915Notes

Reaction equation

HRID 2091915 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:5]2[N:11]=[C:10]([CH2:12][N:13]3[CH2:18][CH2:17][CH:16]([C:19]([OH:22])([CH3:21])[CH3:20])[CH2:15][CH2:14]3)[CH:9]=[CH:8][C:6]=2[N:7]=1.[F:29][C:30]([F:41])([F:40])[C:31]1[NH:35][C:34]2[CH:36]=[CH:37][CH:38]=[CH:39][C:33]=2[N:32]=1>>[O:26]1[CH2:27][CH2:28][N:23]([C:4]2[C:5]3[N:11]=[C:10]([CH2:12][N:13]4[CH2:18][CH2:17][CH:16]([C:19]([OH:22])([CH3:21])[CH3:20])[CH2:15][CH2:14]4)[CH:9]=[CH:8][C:6]=3[N:7]=[C:2]([N:32]3[C:33]4[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=4[N:35]=[C:31]3[C:30]([F:29])([F:41])[F:40])[N:3]=2)[CH2:24][CH2:25]1

Participants

3

Reactant 2

HCID 675602-(Trifluoromethyl)-1H-benzimidazoleHCID 584049702-(1-((2-Chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidin-4-yl)propan-2-ol

Product 1

HCID 533791292-(1-((4-morpholino-2-(2-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)pyrido[3,2-d]pyrimidin-6-yl)methyl)piperidin-4-yl)propan-2-ol

Procedure

Following General Procedure D, 2-(1-((2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidin-4-yl)propan-2-ol from Example 8 was reacted with 2-(trifluoromethyl)-1H-benzo[d]imidazole to give 156. 1H NMR (400 MHz, DMSO) δ 8.20 (d, J=8.6 Hz, 1H), 8.14 (d, J=8.3 Hz, 1H), 7.94 (d, J=8.6 Hz, 2H), 7.56 (t, J=7.5 Hz, 1H), 7.49 (t, J=7.6 Hz, 1H), 4.56 (s, 4H), 4.04 (s, 1H), 3.86-3.79 (m, 4H), 3.75 (s, 2H), 2.93 (d, J=11.0 Hz, 2H), 2.00 (t, J=10.9 Hz, 2H), 1.67 (d, J=12.1 Hz, 2H), 1.38-1.12 (m, 3H), 1.04 (s, 6H). LCMS: 556.3

Sources & evidence

ORD record
ord-5c87c57764324d04ae39a019e6658105
Source dataset
uspto-grants-2013_05
Patent number
US08440651B2

Reaction notes

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