Dimethylformamide → HCID 22611671, 화합물

HRID 1977614

반응식

HRID 1977614 반응식
C(S)C.[H-].[Na+].CN(C=O)C.[S:11]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]=[N:18][N:19]3[CH:24]=[C:23]([C:25]4[CH:30]=[CH:29][C:28]([O:31]C)=[CH:27][CH:26]=4)[CH:22]=[N:21][C:20]=23)=[CH:12]1>O>[S:11]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]=[N:18][N:19]3[CH:24]=[C:23]([C:25]4[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=4)[CH:22]=[N:21][C:20]=23)=[CH:12]1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 6343EthanethiolHCID 24758Sodium hydrideHCID 53294686-(4-Methoxyphenyl)-3-(3-thienyl)-pyrazolo(1,5-a)pyrimidine

생성물 1

HCID 22611671HCID 22611671, 화합물수율 23.4%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
150 °C

실험 절차

Ethanethiol (30 mg, 36 uL) was added dropwise over 1 min to a suspension of sodium hydride (23 mg, 0.98 mmol) in 10 dry DMF (2 mL) under argon. After 15 min, the compound of example 2 (50 mg, 0.16 mmol) was added and the reaction mixture was heated at 150° C. for 1.5 h. The resulting brown solution was cooled, poured into water (25 mL) and washed with ethyl acetate (2×25 mL). The combined organics were dried (Na2SO4), is concentrated, and purified by flash chromatography (40% EtOAc/Hexanes) to give the title compound as a yellow solid [11 mg, 23%, Rf=0.12 (40% EtOAc/Hexanes)]: 1H NMR (CD3OD) δ8.96 (d, 1H, J=2.4Hz), 8.85 (d, 1H, J=2.2Hz), 8.44 (s, 1H), 7.94 (dd, 1H, J=2.9, 1.2Hz), 7.74 (dd, 1H, J=4.9, 1.2Hz), 7.56 (d, 2 H, J=8.8Hz), 7.46 (dd, 1H, J=4.9, 2.9Hz), 6.94 (d, 2H,J=8.6Hz).

후처리

  1. temperatureThe resulting brown solution was cooled
  2. washwashed with ethyl acetate (2×25 mL)
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. concentrationis concentrated
  5. custompurified by flash chromatography (40% EtOAc/Hexanes)

출처 및 근거

ORD 기록
ord-081f7a65d40a47b38d9d9772398f8cd8
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06235741B1

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