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Anisole → N-[(1S,2S)-2-Amino-4,4-difluorocyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide

HRID 1750563
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HRID 1750563 반응식
[F:1][C:2]1([F:29])[CH2:6][C@H:5]([NH:7][C:8](=[O:20])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:15]2[N:19]=[CH:18][CH:17]=[N:16]2)[C@@H:4]([NH:21]S(C(C)(C)C)(=O)=O)[CH2:3]1.C1(OC)C=CC=CC=1.FC(F)(F)S(O)(=O)=O>C(Cl)Cl>[NH2:21][C@H:4]1[CH2:3][C:2]([F:29])([F:1])[CH2:6][C@@H:5]1[NH:7][C:8](=[O:20])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[N:16]=[CH:17][CH:18]=[N:19]1
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참가 물질

5

반응물 3

HCID 7519AnisoleHCID 62406Trifluoromethanesulfonic acidHCID 118308263N-[(1S,2S)-4,4-Difluoro-2-(2-methylpropane-2-sulfonamido)cyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide

생성물 1

HCID 118308058N-[(1S,2S)-2-Amino-4,4-difluorocyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

To a solution of N-[(1S,2S)-4,4-difluoro-2-(2-methylpropane-2-sulfonamido)cyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide (1.7 g, 3.98 mmol) in DCM (100 ml) at 0° C. was added anisole (CAS number 100-66-3; 7.82 ml, 71.6 mmol) followed by the drop wise addition of trifluoromethanesulfonic acid in DCM (0.2M, 1.55 ml, 17.5 mmol). The reaction mixture was stirred at 0° C. for 1 hour and then at room temperature for 18 hours. The reaction mixture was quenched with sodium hydroxide (0.2M) until pH 11 obtained then extracted with DCM. The organics were filtered through a hydrophobic frit and concentrated in vacuo. The crude material was purified by SCX chromatography (2M ammonia in methanol) to afford the title compound.

후처리

  1. waitat room temperature for 18 hours
  2. customThe reaction mixture was quenched with sodium hydroxide (0.2M) until pH 11
  3. customobtained
  4. extractionthen extracted with DCM
  5. filtrationThe organics were filtered through a hydrophobic frit
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by SCX chromatography (2M ammonia in methanol)

출처 및 근거

ORD 기록
ord-0080dfd69fde4876b7fb4fa2481965af
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09156829B2

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