4-Aminotetrahydropyran → 2-Chloro-N-(tetrahydro-2H-pyran-4-yl)thiazole-5-carboxamide

HRID 1923648Notes

Reaction equation

C(O[C:4]([C:6]1[S:10][C:9]([Cl:11])=[N:8][CH:7]=1)=[O:5])C.[NH2:12][CH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>>[O:16]1[CH2:17][CH2:18][CH:13]([NH:12][C:4]([C:6]2[S:10][C:9]([Cl:11])=[N:8][CH:7]=2)=[O:5])[CH2:14][CH2:15]1

Participants

Reactant 2

HCID 4192234-Aminotetrahydropyran

HCID 19017727Ethyl 2-chloro-1,3-thiazole-5-carboxylate

Product 1

HCID 666437572-Chloro-N-(tetrahydro-2H-pyran-4-yl)thiazole-5-carboxamideYield 73%

Procedure

As described for example 135a, 2-chloro-thiazole-5-carboxylic acid ethyl ester (500 mg, 2.6 mmol) was converted, using 4-aminotetrahydropyran instead of isopropylamine, to the title compound (471 mg, 73%) which was obtained as a white solid after purification by chromatography (silica, 0 to 3% methanol in dichloromethane). MS: m/e=247.3 [M+H]+.

Sources & evidence

ORD record: ord-0c1aff949bc64a678c7b9ccbdab7d3c8
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178522B2

Reaction notes

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