Potassium Carbonate → N-(2,4-difluorophenyl)-2-(6-(4-(2-fluorophenyl)piperazine-1-carbonyl)-5-methyl-4-oxothieno[2,3-d]pyrimidin-3(4H)-yl)acetamide

HRID 1094719노트

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HRID 1094719 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[S:25][C:19]3[N:20]=[CH:21][NH:22][C:23](=[O:24])[C:18]=3[C:17]=2[CH3:26])=[O:15])[CH2:10][CH2:9]1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:34][C:35]([NH:37][C:38]1[CH:43]=[CH:42][C:41]([F:44])=[CH:40][C:39]=1[F:45])=[O:36]>CC#N>[F:45][C:39]1[CH:40]=[C:41]([F:44])[CH:42]=[CH:43][C:38]=1[NH:37][C:35](=[O:36])[CH2:34][N:22]1[C:23](=[O:24])[C:18]2[C:17]([CH3:26])=[C:16]([C:14]([N:11]3[CH2:10][CH2:9][N:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[F:1])[CH2:13][CH2:12]3)=[O:15])[S:25][C:19]=2[N:20]=[CH:21]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 7358542-chloro-N-(2,4-difluorophenyl)acetamideHCID 160032576-(4-(2-fluorophenyl)piperazine-1-carbonyl)-5-methylthieno[2,3-d]pyrimidin-4(3H)-one

생성물 1

HCID 59842858N-(2,4-difluorophenyl)-2-(6-(4-(2-fluorophenyl)piperazine-1-carbonyl)-5-methyl-4-oxothieno[2,3-d]pyrimidin-3(4H)-yl)acetamide수율 35%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
130 °C

실험 절차

To a suspension of 6-(4-(2-fluorophenyl)piperazine-1-carbonyl)-5-methylthieno[2,3-d]pyrimidin-4(3H)-one, (0.06 g, 0.16 mmol) in CH3CN (0.5 mL) was added K2CO3 (22 mg, 0.16 mmol), KI (29 mg, 0.17 mmol), and 2-chloro-N-(2,4-difluorophenyl)acetamide, (36 mg, 0.16 mmol). The reaction mixture was heated at 130° C. for 25 min in a microwave reactor. The reaction was quenched with H2O (25 mL) and the aqueous layer was extracted with EtOAc (25 mL). The organic layer was washed with brine (25 mL), dried over Na2SO4 and concentrated. The crude material was purified by flash chromatography (Et2O:DCM, 1:1) providing 30 mg of pure N-(2,4-difluorophenyl)-2-(6-(4-(2-fluorophenyl)piperazine-1-carbonyl)-5-methyl-4-oxothieno[2,3-d]pyrimidin-3(4H)-yl)acetamide, (yield: 35%).

후처리

  1. customThe reaction was quenched with H2O (25 mL)
  2. extractionthe aqueous layer was extracted with EtOAc (25 mL)
  3. washThe organic layer was washed with brine (25 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude material was purified by flash chromatography (Et2O:DCM, 1:1)

출처 및 근거

ORD 기록
ord-f2bb043b49d941cb8cb86831a0ad4fec
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08133998B2

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