Methyl 2-bromo-2-methylpropionate → racemic methyl 2-(4-((2-(2-ethyl-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yl)(hydroxy)methyl)piperidin-1-yl)-2-methylpropanoate

HRID 1946043Notes

Reaction equation

HRID 1946043 reaction equation
[CH2:1]([C:3]1[N:7]([C:8]2[N:16]=[C:15]3[C:11]([N:12]=[C:13]([CH:18]([CH:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)[OH:19])[N:14]3[CH3:17])=[C:10]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[N:9]=2)[C:6]2[CH:32]=[CH:33][CH:34]=[CH:35][C:5]=2[N:4]=1)[CH3:2].[CH3:36][O:37][C:38](=[O:43])[C:39](Br)([CH3:41])[CH3:40]>>[CH2:1]([C:3]1[N:7]([C:8]2[N:16]=[C:15]3[C:11]([N:12]=[C:13]([CH:18]([OH:19])[CH:20]4[CH2:21][CH2:22][N:23]([C:39]([CH3:41])([CH3:40])[C:38]([O:37][CH3:36])=[O:43])[CH2:24][CH2:25]4)[N:14]3[CH3:17])=[C:10]([N:26]3[CH2:27][CH2:28][O:29][CH2:30][CH2:31]3)[N:9]=2)[C:6]2[CH:32]=[CH:33][CH:34]=[CH:35][C:5]=2[N:4]=1)[CH3:2]

Participants

3

Reactant 2

HCID 90097Methyl 2-bromo-2-methylpropionateHCID 59605474(2-(2-ethyl-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yl)(piperidin-4-yl)methanol

Product 1

HCID 59606022racemic methyl 2-(4-((2-(2-ethyl-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yl)(hydroxy)methyl)piperidin-1-yl)-2-methylpropanoateYield 83%

Procedure

Following General Procedure C, (2-(2-ethyl-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yl)(piperidin-4-yl)methanol was alkylated with 2-bromo-2-methylpropionic acid methyl ester to give the racemate desired product (0.22 g, 83%). The enantiomers were separated by SFC to give 526. LCMS m/z: 289.2 (2M+H+)

Sources & evidence

ORD record
ord-d2b25071c37e41bb9d0dad8384b42830
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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