Piperidin-4-yl pivalate → 4-(5-Chloro-benzofuran-3-ylmethoxy)-1H-indole-2-carboxylic acid {4-[2-(4-hydroxy-piperidin-1-yl)-ethyl]-phenyl}-amide

HRID 2267933Notes

Reaction equation

HRID 2267933 reaction equation
O[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[NH:14][C:15]3[C:20]([CH:21]=2)=[C:19]([O:22][CH2:23][C:24]2[C:28]4[CH:29]=[C:30]([Cl:33])[CH:31]=[CH:32][C:27]=4[O:26][CH:25]=2)[CH:18]=[CH:17][CH:16]=3)=[O:12])=[CH:6][CH:5]=1.[NH:34]1[CH2:39][CH2:38][CH:37]([O:40]C(=O)C(C)(C)C)[CH2:36][CH2:35]1>>[OH:40][CH:37]1[CH2:36][CH2:35][N:34]([CH2:2][CH2:3][C:4]2[CH:5]=[CH:6][C:7]([NH:10][C:11]([C:13]3[NH:14][C:15]4[C:20]([CH:21]=3)=[C:19]([O:22][CH2:23][C:24]3[C:28]5[CH:29]=[C:30]([Cl:33])[CH:31]=[CH:32][C:27]=5[O:26][CH:25]=3)[CH:18]=[CH:17][CH:16]=4)=[O:12])=[CH:8][CH:9]=2)[CH2:39][CH2:38]1

Participants

3

Reactant 2

HCID 57464983Piperidin-4-yl pivalateHCID 66841637HCID 66841637, compound

Product 1

HCID 596001444-(5-Chloro-benzofuran-3-ylmethoxy)-1H-indole-2-carboxylic acid {4-[2-(4-hydroxy-piperidin-1-yl)-ethyl]-phenyl}-amide

Procedure

This compound is synthesized analogously to example 154 from 4-(5-Chloro-benzofuran-3-ylmethoxy)-1H-indole-2-carboxylic acid [4-(2-hydroxy-ethyl)-phenyl]-amide (193) and 2,2-dimethyl-propionic acid piperidin-4-yl ester, followed by removal of the protective group by sodium methylate.

Workup

  1. customfollowed by removal of the protective group by sodium methylate

Sources & evidence

ORD record
ord-c995516de0594922961d08c8387f37f5
Source dataset
uspto-grants-2010_12
Patent number
US07858781B2

Reaction notes

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