Piperidine → 1-Methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carboxylic acid [2-(2-amino-ethoxy)-ethyl]-amide

HRID 410987Notes

Reaction equation

HRID 410987 reaction equation
C1C2C(COC(=O)[NH:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][NH:23][C:24]([C:26]3[CH:50]=[CH:49][C:29]4[N:30]([CH3:48])[C:31]([NH:33][C:34]5[S:35][C:36]6[CH:42]=[C:41]([O:43][C:44]([F:47])([F:46])[F:45])[CH:40]=[CH:39][C:37]=6[N:38]=5)=[N:32][C:28]=4[CH:27]=3)=[O:25])C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>CN(C=O)C>[NH2:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][NH:23][C:24]([C:26]1[CH:50]=[CH:49][C:29]2[N:30]([CH3:48])[C:31]([NH:33][C:34]3[S:35][C:36]4[CH:42]=[C:41]([O:43][C:44]([F:45])([F:46])[F:47])[CH:40]=[CH:39][C:37]=4[N:38]=3)=[N:32][C:28]=2[CH:27]=1)=[O:25]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 86656900HCID 86656900, compound

Product 1

HCID 866569011-Methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carboxylic acid [2-(2-amino-ethoxy)-ethyl]-amideYield 95.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carboxylic acid [2-(2-amino-ethoxy)-ethyl]-amide (70 mg) was prepared by following General Procedure 0 starting from [2-(2-{[1-methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carbonyl]-amino}-ethoxy)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester (106 mg), 20% (v/v) piperidine in DMF (1.5 mL). LC/MS: m/z 494.5.

Sources & evidence

ORD record
ord-97590f95e950420081619947a74867a5
Source dataset
uspto-grants-2014_06
Patent number
US08759535B2

Reaction notes

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