LiOH THF → 2-(4-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-4-[(2-methoxyethoxy)methyl]-1,3-thiazole-5-carboxylic acid

HRID 2234007Notes

Reaction equation

HRID 2234007 reaction equation
Cl.[NH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[S:10][C:11]([C:20]([O:22]CC)=[O:21])=[C:12]([CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])[N:13]=2)[CH2:5][CH2:4]1.[Cl:25][C:26]1[C:30]([Cl:31])=[C:29]([CH3:32])[NH:28][C:27]=1[C:33](NC1CCN(C2SC(C3NN=NN=3)=CN=2)CC1)=[O:34].[Li+].[OH-].C1COCC1>>[Cl:25][C:26]1[C:30]([Cl:31])=[C:29]([CH3:32])[NH:28][C:27]=1[C:33]([NH:2][CH:3]1[CH2:4][CH2:5][N:6]([C:9]2[S:10][C:11]([C:20]([OH:22])=[O:21])=[C:12]([CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])[N:13]=2)[CH2:7][CH2:8]1)=[O:34]

Participants

4

Reactant 3

HCID 67059675LiOH THFHCID 68579915Ethyl 2-(4-aminopiperidin-1-yl)-4-[(2-methoxyethoxy)methyl]-1,3-thiazole-5-carboxylate hydrochloride2×HCID 178433654HCID 178433654, compound2×

Product 1

HCID 685797112-(4-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-4-[(2-methoxyethoxy)methyl]-1,3-thiazole-5-carboxylic acid

Procedure

Prepared in an analogous manner to Example 129 starting from ethyl 2-(4-aminopiperidin-1-yl)-4-[(2-methoxyethoxy)methyl]-1,3-thiazole-5-carboxylate hydrochloride (Intermediate 126) and 3,4-dichloro-5-methyl-1H-pyrrole-2-carboxylic acid (Intermediate 3). The ester product was submitted to hydrolysis using LiOH/THF at 65° C.

Workup

  1. customat 65° C.

Sources & evidence

ORD record
ord-256b3800db2e4e91916e86c6e50ef883
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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