Potassium Carbonate → 2-(3-((3-((4-(Piperidin-1-yl)-2-((1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-3-yl)carbamoyl)phenyl)carbamoyl)benzyl)thio)phenyl)acetic acid

HRID 2409871노트

반응식

HRID 2409871 반응식
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:39]=[CH:40][CH:41]=1)[C:6]([NH:8][C:9]1[CH:32]=[CH:31][C:30]([N:33]2[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)=[CH:29][C:10]=1[C:11]([NH:13][C:14]1[CH:18]=[CH:17][N:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)[N:15]=1)=[O:12])=[O:7].C(=O)([O-])[O-].[K+].[K+].[SH:48][C:49]1[CH:50]=[C:51]([CH2:55][C:56]([OH:58])=[O:57])[CH:52]=[CH:53][CH:54]=1>CN(C=O)C>[N:33]1([C:30]2[CH:31]=[CH:32][C:9]([NH:8][C:6]([C:5]3[CH:4]=[C:3]([CH:41]=[CH:40][CH:39]=3)[CH2:2][S:48][C:49]3[CH:50]=[C:51]([CH2:55][C:56]([OH:58])=[O:57])[CH:52]=[CH:53][CH:54]=3)=[O:7])=[C:10]([C:11](=[O:12])[NH:13][C:14]3[CH:18]=[CH:17][N:16]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:27])([F:28])[F:26])[CH:20]=4)[N:15]=3)[CH:29]=2)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 35431562-(3-Mercaptophenyl)acetic acid2회HCID 665882652-(3-(chloromethyl)benzamido)-5-(piperidin-1-yl)-N-(1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-3-yl)benzamide

생성물 1

HCID 566445522-(3-((3-((4-(Piperidin-1-yl)-2-((1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-3-yl)carbamoyl)phenyl)carbamoyl)benzyl)thio)phenyl)acetic acid

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Into a round bottom flask was placed a solution of 2-(3-(chloromethyl)benzamido)-5-(piperidin-1-yl)-N-(1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-3-yl)benzamide 21b (0.23 mmol, 1 equiv) in DMF (1.2 mL), potassium carbonate (127.1 mg, 0.92 mmol, 4 equiv), and (3-mercaptophenyl)acetic acid (42.6 mg, 0.253 mmol, 1.1 equiv). The solution was stirred overnight at room temperature. The reaction progress was monitored by LCMS. After 16.5 h, more (3-mercaptophenyl)acetic acid (7 mg) was added to the solution, and the solution was stirred another 1 h. The solvent was removed. The residue was dissolved with DCM, washed with H2O and brine, and dried over sodium sulfate. The product was purified by reverse phase HPLC, eluting with 0.05% TFA in a water/acetonitrile gradient. MS (ES, m/z) 714 [M+H]+.

후처리

  1. customInto a round bottom flask was placed
  2. waitAfter 16.5 h
  3. stirringthe solution was stirred another 1 h
  4. customThe solvent was removed
  5. dissolutionThe residue was dissolved with DCM
  6. washwashed with H2O and brine
  7. dry with materialdried over sodium sulfate
  8. customThe product was purified by reverse phase HPLC
  9. washeluting with 0.05% TFA in a water/acetonitrile gradient

출처 및 근거

ORD 기록
ord-dbeb1e09a6ee4a8d9b138e3856721257
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815910B2

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