Ethyl 2-(5-bromopyridin-3-yl)acetate → (5-{4-benzylcarbamoyl-2-[(N-benzyl-N-cyclopropanecarbonyl-amino)-methyl]-phenyl}-pyridin-3-yl)-acetic acid ethyl ester

HRID 554600Notes

Reaction equation

HRID 554600 reaction equation
[CH2:1]([NH:8][C:9](=[O:39])[C:10]1[CH:15]=[CH:14][C:13](B2OC(C)(C)C(C)(C)O2)=[C:12]([CH2:25][N:26]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]([CH:29]2[CH2:31][CH2:30]2)=[O:28])[CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:40]([O:42][C:43](=[O:52])[CH2:44][C:45]1[CH:46]=[N:47][CH:48]=[C:49](Br)[CH:50]=1)[CH3:41]>>[CH2:40]([O:42][C:43](=[O:52])[CH2:44][C:45]1[CH:46]=[N:47][CH:48]=[C:49]([C:13]2[CH:14]=[CH:15][C:10]([C:9](=[O:39])[NH:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:11][C:12]=2[CH2:25][N:26]([CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:27]([CH:29]2[CH2:31][CH2:30]2)=[O:28])[CH:50]=1)[CH3:41]

Participants

3

Reactant 2

HCID 54116619Ethyl 2-(5-bromopyridin-3-yl)acetateHCID 67212540HCID 67212540, compound

Product 1

HCID 67212484(5-{4-benzylcarbamoyl-2-[(N-benzyl-N-cyclopropanecarbonyl-amino)-methyl]-phenyl}-pyridin-3-yl)-acetic acid ethyl ester

Procedure

N-Benzyl-3-[(N-benzyl-N-cyclopropanecarbonyl-amino)-methyl]-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide and (5-bromo-pyridin-3-yl)-acetic acid ethyl ester were reacted as described in Example 3, Step 6 to provide (5-{4-benzylcarbamoyl-2-[(N-benzyl-N-cyclopropanecarbonyl-amino)-methyl]-phenyl}-pyridin-3-yl)-acetic acid ethyl ester.

Sources & evidence

ORD record
ord-d322498a59a74271a5cdd9ed9262ebf6
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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