Diisopropylethylamine → 2-{4-[1-(3,5-Diethoxy-4-pyrrol-1-yl-benzyl)-piperidin-4-ylcarbamoyl]-phenyl}-2-methyl-propionic acid methyl ester

HRID 502401Notes

Reaction equation

HRID 502401 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]([CH3:21])([C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:20])[NH:13][CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:8][CH:7]=1)[CH3:5].[CH2:23]([O:25][C:26]1[CH:27]=[C:28]([CH:31]=[C:32]([O:39][CH2:40][CH3:41])[C:33]=1[N:34]1[CH:38]=[CH:37][CH:36]=[CH:35]1)[CH:29]=O)[CH3:24].C([BH3-])#N.[Na+].C(N(C(C)C)C(C)C)C>C(O)C.C(O)(=O)C>[CH3:1][O:2][C:3](=[O:22])[C:4]([C:6]1[CH:7]=[CH:8][C:9]([C:12](=[O:20])[NH:13][CH:14]2[CH2:15][CH2:16][N:17]([CH2:29][C:28]3[CH:31]=[C:32]([O:39][CH2:40][CH3:41])[C:33]([N:34]4[CH:38]=[CH:37][CH:36]=[CH:35]4)=[C:26]([O:25][CH2:23][CH3:24])[CH:27]=3)[CH2:18][CH2:19]2)=[CH:10][CH:11]=1)([CH3:5])[CH3:21]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5003444Sodium cyanoborohydrideHCID 534860133,5-diethoxy-4-(1H-pyrrol-1-yl)benzaldehydeHCID 684593812-Methyl-2-[4-(piperidin-4-ylcarbamoyl)-phenyl]-propionic acid methyl ester

Product 1

HCID 684579272-{4-[1-(3,5-Diethoxy-4-pyrrol-1-yl-benzyl)-piperidin-4-ylcarbamoyl]-phenyl}-2-methyl-propionic acid methyl ester

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

In analogy to the procedure described in example 50k), 2-methyl-2-[4-(piperidin-4-ylcarbamoyl)-phenyl]-propionic acid methyl ester (example 60e) was reacted with 3,5-diethoxy-4-pyrrol-1-yl-benzaldehyde (example 40b), sodium cyanoborohydride, N-ethyl-diisopropylamine and acetic acid in ethanol at 50° C. to yield the title compound as light yellow foam. MS: 548.4 (MH+).

Sources & evidence

ORD record
ord-35c55216ecea468e9f02faf2609604ca
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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