Ethyl 2-(4-bromobenzyl)benzoate → Ethyl 2-{4-[4-({5-(benzyloxy)-4-[(2-tert-butoxy-2-oxoethyl)carbamoyl]-6-methylpyrimidin-2-yl}methyl)piperidin-1-yl]benzyl}benzoate

HRID 1626806Notes

Reaction equation

HRID 1626806 reaction equation
Cl.[CH2:2]([O:9][C:10]1[C:11]([C:24]([NH:26][CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[O:25])=[N:12][C:13]([CH2:17][CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[N:14][C:15]=1[CH3:16])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[C:36]1[CH:53]=[CH:52][C:39]([CH2:40][C:41]2[CH:51]=[CH:50][CH:49]=[CH:48][C:42]=2[C:43]([O:45][CH2:46][CH3:47])=[O:44])=[CH:38][CH:37]=1>>[CH2:2]([O:9][C:10]1[C:11]([C:24](=[O:25])[NH:26][CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[N:12][C:13]([CH2:17][CH:18]2[CH2:19][CH2:20][N:21]([C:36]3[CH:53]=[CH:52][C:39]([CH2:40][C:41]4[CH:51]=[CH:50][CH:49]=[CH:48][C:42]=4[C:43]([O:45][CH2:46][CH3:47])=[O:44])=[CH:38][CH:37]=3)[CH2:22][CH2:23]2)=[N:14][C:15]=1[CH3:16])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 68193210Ethyl 2-(4-bromobenzyl)benzoateHCID 86670085Tert-butyl ({[5-(benzyloxy)-6-methyl-2-(piperidin-4-ylmethyl)pyrimidin-4-yl]carbonyl}amino)acetate hydrochloride

Product 1

HCID 68193257Ethyl 2-{4-[4-({5-(benzyloxy)-4-[(2-tert-butoxy-2-oxoethyl)carbamoyl]-6-methylpyrimidin-2-yl}methyl)piperidin-1-yl]benzyl}benzoateYield 72%

Procedure

In accordance with Example 1-(9), but using tert-butyl ({[5-(benzyloxy)-6-methyl-2-(piperidin-4-ylmethyl)pyrimidin-4-yl]carbonyl}amino)acetate hydrochloride instead of tert-butyl 5-(benzyloxy)-6-methyl-2-(piperidin-4-ylmethyl)pyrimidine-4-carboxylate hydrochloride, and ethyl 2-(4-bromobenzyl)benzoate instead of [(4′-bromobiphenyl-4-yl)methoxy](tert-butyl)dimethylsilane, the title compound (yield 72%) was afforded as a white solid.

Sources & evidence

ORD record
ord-874e7e09a35240f89f2919ade0d19d86
Source dataset
uspto-grants-2014_07
Patent number
US08785462B2

Reaction notes

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