2-(difluoromethyl)-1H-1,3-benzodiazole → HCID 53379130, compound

HRID 1043643Notes

Reaction equation

HRID 1043643 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][CH:30]([F:40])[C:31]1[NH:35][C:34]2[CH:36]=[CH:37][CH:38]=[CH:39][C:33]=2[N:32]=1>>[F:40][CH:30]([F:29])[C:31]1[N:32]([C:2]2[N:3]=[C:4]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[C:5]3[N:11]=[C:10]([CH2:12][N:13]4[CH2:14][CH2:15][CH:16]([C:19]([OH:22])([CH3:20])[CH3:21])[CH2:17][CH2:18]4)[CH:9]=[CH:8][C:6]=3[N:7]=2)[C:33]2[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=2[N:35]=1

Participants

3

Reactant 2

HCID 5977032-(difluoromethyl)-1H-1,3-benzodiazoleHCID 584049702-(1-((2-Chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidin-4-yl)propan-2-ol

Product 1

HCID 53379130HCID 53379130, compound

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-(difluoromethyl)-1H-benzo[d]imidazole to give 157. 1H NMR (400 MHz, DMSO) δ 8.43 (d, J=8.3 Hz, 1H), 8.23 (d, J=8.7 Hz, 1H), 8.00-7.72 (overlapping m, 3H), 7.51 (app t, J=7.7 Hz, 1H), 7.44 (app t, J=7.7 Hz, 1H), 4.56 (br s, 4H), 4.03 (s, 1H), 3.86 (br s, 4H), 3.74 (br s, 2H), 2.92 (d, J=10.6 Hz, 2H), 1.99 (t, J=11.3 Hz, 2H), 1.67 (d, J=11.8 Hz, 2H), 1.38-1.10 (overlapping m, 3H), 1.04 (s, 6H). LCMS: 538.3

Sources & evidence

ORD record
ord-45086f8e61034acbba336d7210c0f1f5
Source dataset
uspto-grants-2013_10
Patent number
US08563540B2

Reaction notes

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