Tetrahydrofuran → HCID 66832128, 화합물

HRID 58773노트

반응식

[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:19][C:20]1[CH:21]=[C:22]2[C:28]([CH2:29][CH2:30][NH:31][C:32]([C:34]3[CH:38]=[C:37]([CH2:39][C:40]4[CH:45]=[C:44]([F:46])[CH:43]=[CH:42][C:41]=4[F:47])[O:36][N:35]=3)=[O:33])=[C:27]([Si](CC)(CC)CC)[NH:26][C:23]2=[N:24][CH:25]=1.C1C[O:58]CC1>>[Cl:19][C:20]1[CH:21]=[C:22]2[C:28]([CH2:29][CH2:30][NH:31][C:32]([C:34]3[CH:38]=[C:37]([C:39](=[O:58])[C:40]4[CH:45]=[C:44]([F:46])[CH:43]=[CH:42][C:41]=4[F:47])[O:36][N:35]=3)=[O:33])=[CH:27][NH:26][C:23]2=[N:24][CH:25]=1

참가 물질

반응물 3

HCID 8028Tetrahydrofuran2회

HCID 2724141Tetrabutylammonium Fluoride

HCID 66832015N-(2-(5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethyl)-5-(2,5-difluorobenzyl)isoxazole-3-carboxamide

생성물 1

HCID 66832128HCID 66832128, 화합물수율 22%

실험 절차

A solution of tetrabutylammonium fluoride 1M in THF (1 mL; 1 mmol) was added to a solution of N-(2-(5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethyl)-5-(2,5-difluorobenzyl)isoxazole-3-carboxamide (0.105 g, 0.198 mmol) in THF (5 mL). The mixture was stirred overnight at room temperature and was evaporated. The residue was dissolved in dichloromethane, and the organic solution was washed with water and was concentrated under reduced pressure. The crude material was purified twice by flash chromatography on silica gel (eluent: 0 to 40% of ethyl acetate in dichloromethane) to give 0.019 g (22%) of N-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)ethyl)-5-(2,5-difluorobenzoyl)isoxazole-3-carboxamide as a white solid.

후처리

customwas evaporated
dissolutionThe residue was dissolved in dichloromethane
washthe organic solution was washed with water
concentrationwas concentrated under reduced pressure
customThe crude material was purified twice by flash chromatography on silica gel (eluent: 0 to 40% of ethyl acetate in dichloromethane)

출처 및 근거

ORD 기록: ord-5cc08393b6654dfd95d5f247c4584ce9
출처 데이터셋: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US09434722B2

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