Propanamide, 3,3,3-trifluoro-N-(4-mercaptophenyl)- → HCID 178428352, 화합물

HRID 499088노트

반응식

HRID 499088 반응식
[CH:1]1([C:4]2([F:26])[CH2:7][N:6]([C:8]3[N:13]=[C:12]([S:14]([CH3:17])(=O)=O)[N:11]=[C:10]([NH:18][C:19]4[NH:23][N:22]=[C:21]([CH3:24])[CH:20]=4)[C:9]=3[F:25])[CH2:5]2)[CH2:3][CH2:2]1.[F:27][C:28]([F:41])([F:40])[CH2:29][C:30]([NH:32][C:33]1[CH:38]=[CH:37]C(S)=[CH:35][CH:34]=1)=[O:31]>CN(C=O)C.C(OC(=O)C)C.C([O-])(O)=O.[Na+]>[CH3:24][C:21]1[CH:20]=[C:19]([NH:18][C:10]2[C:9]([F:25])=[C:8]([N:6]3[CH2:7][C:4]([CH:1]4[CH2:3][CH2:2]4)([F:26])[CH2:5]3)[N:13]=[C:12]([S:14][C:17]3[CH:35]=[CH:34][C:33]([NH:32][C:30](=[O:31])[CH2:29][C:28]([F:41])([F:27])[F:40])=[CH:38][CH:37]=3)[N:11]=2)[NH:23][N:22]=1

참가 물질

6

반응물 2

HCID 57674932Propanamide, 3,3,3-trifluoro-N-(4-mercaptophenyl)-HCID 178428354HCID 178428354, 화합물

생성물 1

HCID 178428352HCID 178428352, 화합물수율 44.9%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매HCID 516892Sodium Bicarbonate용매

실험 절차

A solution of 6-(3-cyclopropyl-3-fluoroazetidin-1-yl)-5-fluoro-N-(3-methyl-1H-pyrazol-5-yl)-2-(methylsulfonyl)pyrimidin-4-amine (64 mg, 0.17 mmol) and 3,3,3-trifluoro-N-(4-mercaptophenyl)propanamide (47 mg, 0.20 mmol) in DMF (3 ml) was heated to 80° C. and stirred for 6 hrs. The reaction was diluted with ethylacetate (20 ml) and Sat. NaHCO3 (20 ml) and the organic layer washed with brine (20 ml), dried (Na2SO4) and concentrated to give an oil. Compound was purified by mass directed preparative HPLC, eluted with acetonitrile/water/TFA to give the title compound as a white solid (TFA salt, 41.2 mg, 37%). 1H NMR (DMSO, 400 MHz) 0.46-0.50 (2H, m), 0.61-0.64 (2H, m), 1.38-1.45 (1H, m), 1.93 (3H, s), 3.55 (2H, q), 4.00-4.18 (4H, m), 5.27 (1H, s), 7.54 (2H, d), 7.71 (2H, d), 9.39 (1H, s), 10.57 (1H, s). ES+ 540.

후처리

  1. washthe organic layer washed with brine (20 ml)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customto give an oil
  5. customCompound was purified by mass
  6. washeluted with acetonitrile/water/TFA

출처 및 근거

ORD 기록
ord-9dba89fc3e0346ac87aee0a4100a42d4
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07767672B2

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