Diisopropylethylamine → N-(1-cyanocyclopropyl)-3-(2-difluoromethoxyphenylmethanesulfonyl)-2(R)-[2,2,2-trifluoro-1 (s)-(4-fluorophenyl)ethylamino]propionamide

HRID 17012노트

반응식

HRID 17012 반응식
[F:1][CH:2]([F:32])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][S:11]([CH2:14][C@H:15]([NH:19][CH:20]([C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)[C:21]([F:24])([F:23])[F:22])[C:16]([OH:18])=O)(=[O:13])=[O:12].Cl.[NH2:34][C:35]1([C:38]#[N:39])[CH2:37][CH2:36]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[C:38]([C:35]1([NH:34][C:16](=[O:18])[C@@H:15]([NH:19][C@@H:20]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[C:21]([F:23])([F:22])[F:24])[CH2:14][S:11]([CH2:10][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[O:3][CH:2]([F:1])[F:32])(=[O:13])=[O:12])[CH2:37][CH2:36]1)#[N:39]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 145863631-Amino-1-cyclopropanecarbonitrile hydrochlorideHCID 866002683-(2-difluoromethoxyphenylmethanesulfonyl)-2(R)-[2,2,2-trifluoro-1(RS)-(4-fluorophenyl)ethylamino]propionic acid

생성물 1

HCID 11387282N-(1-cyanocyclopropyl)-3-(2-difluoromethoxyphenylmethanesulfonyl)-2(R)-[2,2,2-trifluoro-1 (s)-(4-fluorophenyl)ethylamino]propionamide수율 70%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-(2-difluoromethoxyphenylmethanesulfonyl)-2(R)-[2,2,2-trifluoro-1(RS)-(4-fluorophenyl)ethylamino]propionic acid (157 mg, 0.325 mmol) in DMF (5 mL) was added 1-aminocyclopropanecarbonitrile hydrochloride (46.4 mg, 0.39 mmol), HATU (186.3 mg, 0.49 mmol) and DIPEA (63.2 mg, 0.49 mmol). After 1 h, the reaction mixture was extracted with ethyl acetate (100 mL) and washed with satured NaHCO3 and brine. After drying with MgSO4, the solvent was removed and the residue was purified by column chromatograph yield the title compound (125 mg).

후처리

  1. extractionthe reaction mixture was extracted with ethyl acetate (100 mL)
  2. washwashed with satured NaHCO3 and brine
  3. dry with materialAfter drying with MgSO4
  4. customthe solvent was removed
  5. customthe residue was purified by column chromatograph

출처 및 근거

ORD 기록
ord-79feb1fd073743ba97cadb4a2d46460b
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737300B2

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