2-(propan-2-yl)-1H-1,3-benzodiazole → tert-butyl 3-hydroxy-3-(2-(2-isopropyl-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yl)piperidine-1-carboxylate

HRID 1923276Notes

Reaction equation

HRID 1923276 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([C:12]3([OH:25])[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]3)[N:8]2[CH3:11])=[C:4]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[N:3]=1.[CH:32]([C:35]1[NH:36][C:37]2[CH:43]=[CH:42][CH:41]=[CH:40][C:38]=2[N:39]=1)([CH3:34])[CH3:33]>>[OH:25][C:12]1([C:7]2[N:8]([CH3:11])[C:9]3[C:5]([N:6]=2)=[C:4]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[N:3]=[C:2]([N:36]2[C:37]4[CH:43]=[CH:42][CH:41]=[CH:40][C:38]=4[N:39]=[C:35]2[CH:32]([CH3:34])[CH3:33])[N:10]=3)[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:13]1

Participants

3

Reactant 2

HCID 221212-(propan-2-yl)-1H-1,3-benzodiazoleHCID 59605825tert-butyl 3-(2-chloro-9-methyl-6-morpholino-9H-purin-8-yl)-3-hydroxypiperidine-1-carboxylate

Product 1

HCID 59605652tert-butyl 3-hydroxy-3-(2-(2-isopropyl-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yl)piperidine-1-carboxylate

Procedure

tert-Butyl 3-(2-chloro-9-methyl-6-morpholino-9H-purin-8-yl)-3-hydroxypiperidine-1-carboxylate (1 g) was reacted with 2-isopropylbenzimidazole via General Procedure I for Buchwald coupling to give 0.65 g of tert-butyl 3-hydroxy-3-(2-(2-isopropyl-1H-benzo [d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yl)piperidine-1-carboxylate following flash column chromatography.

Sources & evidence

ORD record
ord-069554170d5b46b385fa1c4477bba6e7
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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