Benzimidazole → 2-(4-((2-(2-(1,1-difluoroethyl)-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yl)methyl)piperazin-1-yl)-2-methylpropan-1-ol

HRID 1945994Notes

Reaction equation

HRID 1945994 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.Cl[C:11]1[N:19]=[C:18]2[C:14]([N:15]=[C:16]([CH2:21][N:22]3[CH2:27][CH2:26][N:25]([C:28]([CH3:32])([CH3:31])[CH2:29][OH:30])[CH2:24][CH2:23]3)[N:17]2[CH3:20])=[C:13]([N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)[N:12]=1.[F:39][CH:40]([F:44])[C:41](O)=O>>[F:39][C:40]([C:2]1[N:3]([C:11]2[N:19]=[C:18]3[C:14]([N:15]=[C:16]([CH2:21][N:22]4[CH2:27][CH2:26][N:25]([C:28]([CH3:32])([CH3:31])[CH2:29][OH:30])[CH2:24][CH2:23]4)[N:17]3[CH3:20])=[C:13]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)[N:12]=2)[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:1]=1)([F:44])[CH3:41]

Participants

4

Reactant 3

HCID 5798BenzimidazoleHCID 9788Difluoroacetic acidHCID 866482512-(4-((2-chloro-9-methyl-6-morpholino-9H-purin-8-yl)methyl)piperazin-1-yl)-2-methylpropan-1-ol

Product 1

HCID 596055652-(4-((2-(2-(1,1-difluoroethyl)-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yl)methyl)piperazin-1-yl)-2-methylpropan-1-ol

Procedure

Following General Procedure J for Multi-Step Benzimidazole formation, 2-(4-((2-chloro-9-methyl-6-morpholino-9H-purin-8-yl)methyl)piperazin-1-yl)-2-methylpropan-1-ol was converted to 473 with difluoroacetic acid. LCMS: M+H+=570.3

Sources & evidence

ORD record
ord-e312c66a66924680ac3e9a8bc3708a16
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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