Potassium Carbonate → 3-{[4-(Azetidin-1-ylcarbonyl)-2-chlorophenyl]oxy}-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}N-(1-methyl-1H-pyrazol-3-yl)benzamide

HRID 20512노트

반응식

HRID 20512 반응식
[Si]([O:8][CH2:9][C@H:10]([CH3:28])[O:11][C:12]1[CH:13]=[C:14]([CH:24]=[C:25]([OH:27])[CH:26]=1)[C:15]([NH:17][C:18]1[CH:22]=[CH:21][N:20]([CH3:23])[N:19]=1)=[O:16])(C(C)(C)C)(C)C.[Cl:29][C:30]1[CH:31]=[C:32]([CH:39]=[CH:40][C:41]=1F)[C:33]([N:35]1[CH2:38][CH2:37][CH2:36]1)=[O:34].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N:35]1([C:33]([C:32]2[CH:39]=[CH:40][C:41]([O:27][C:25]3[CH:24]=[C:14]([CH:13]=[C:12]([O:11][C@@H:10]([CH3:28])[CH2:9][OH:8])[CH:26]=3)[C:15]([NH:17][C:18]3[CH:22]=[CH:21][N:20]([CH3:23])[N:19]=3)=[O:16])=[C:30]([Cl:29])[CH:31]=2)=[O:34])[CH2:38][CH2:37][CH2:36]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 536296323-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]-5-hydroxy-N-(1-methyl-1H-pyrazol-3-yl)benzamideHCID 59346868(Azetidin-1-yl)(3-chloro-4-fluorophenyl)methanone

생성물 1

HCID 115839093-{[4-(Azetidin-1-ylcarbonyl)-2-chlorophenyl]oxy}-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}N-(1-methyl-1H-pyrazol-3-yl)benzamide수율 50.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
160 °C

실험 절차

To a mixture of 3-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyloxy)-5-hydroxy-N-(1-methyl-1H-pyrazol-3-yl)benzamide (215 mg, 0.53 mmol) and 1-(3-chloro-4-fluorobenzoyl)azetidine (135 mg, 0.63 mmol) in DMF (2.0 mL) was added potassium carbonate (146 mg, 1.06 mmol) and the stirred mixture heated at 160° C. in a ‘Smith Creator Microwave’ for 120 minutes. The mixture was allowed to reach ambient temperature and pressure then reduced in volume. Purification by column chromatography, eluting with 0-20% methanol in DCM, afforded the title compound (130 mg).

후처리

  1. customto reach ambient temperature
  2. customPurification by column chromatography
  3. washeluting with 0-20% methanol in DCM

출처 및 근거

ORD 기록
ord-4743b5858cab40b8ba84b36945f18bf5
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745475B2

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