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Piperidine → 3-Amino-oxetane-3-carboxylic acid {(S)-5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-indan-1-yl}-amide

HRID 2046598
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인쇄 미리보기

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HRID 2046598 반응식
C1C2C(COC(=O)[NH:17][C:18]3([C:22](=[O:47])[NH:23][C@@H:24]4[C:32]5[C:27](=[CH:28][C:29]([C:33]6[CH:38]=[C:37]([Cl:39])[CH:36]=[C:35]([F:40])[C:34]=6[C:41]6[N:45]=[C:44]([CH3:46])[O:43][N:42]=6)=[CH:30][CH:31]=5)[CH2:26][CH2:25]4)[CH2:21][O:20][CH2:19]3)C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>C(Cl)Cl>[Cl:39][C:37]1[CH:36]=[C:35]([F:40])[C:34]([C:41]2[N:45]=[C:44]([CH3:46])[O:43][N:42]=2)=[C:33]([C:29]2[CH:28]=[C:27]3[C:32](=[CH:31][CH:30]=2)[C@@H:24]([NH:23][C:22]([C:18]2([NH2:17])[CH2:19][O:20][CH2:21]2)=[O:47])[CH2:25][CH2:26]3)[CH:38]=1
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참가 물질

4

반응물 2

HCID 8082PiperidineHCID 68296802(3-{(S)-5-[5-Chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-indan-1-ylcarbamoyl}-oxetan-3-yl)-carbamic acid 9H-fluoren-9-ylmethyl ester

생성물 1

HCID 601410403-Amino-oxetane-3-carboxylic acid {(S)-5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-indan-1-yl}-amide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (3-{(S)-5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-indan-1-ylcarbamoyl}-oxetan-3-yl)-carbamic acid 9H-fluoren-9-ylmethyl ester (intermediate A-12) (2.94 g, 4.42 mmol) in MeCl2 (50.0 ml) was added piperidine (4.38 ml) and the mixture was stirred at room temperature for 15 h. The colorless solution was concentrated to dryness under high vacuum at RT. The remaining residue was purified by chromatography (silica gel; MeCl2/MeOH 100:0-95:5) and the title compound was obtained as light brown oil (1.09 g, 56%). MS: 443.1 (MH+, 1Cl).

후처리

  1. concentrationThe colorless solution was concentrated to dryness under high vacuum at RT
  2. customThe remaining residue was purified by chromatography (silica gel; MeCl2/MeOH 100:0-95:5)

출처 및 근거

ORD 기록
ord-fe591d7b037b415197032ccb6fc07c31
출처 데이터셋
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08592426B2

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