Dimethylformamide → 1-(2-Aminopyrimidin-4-yl)-6-bromoindazole-3-carboxamide

HRID 1398578노트

반응식

HRID 1398578 반응식
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([Br:17])[CH:15]=3)[C:10]([C:18]([OH:20])=O)=[N:9]2)[CH:5]=[CH:4][N:3]=1.S(Cl)(Cl)=O.C[N:26](C=O)C>C(Cl)Cl>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([Br:17])[CH:15]=3)[C:10]([C:18]([NH2:26])=[O:20])=[N:9]2)[CH:5]=[CH:4][N:3]=1

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 681819661-(2-Aminopyrimidin-4-yl)-6-bromoindazole-3-carboxylic acid

생성물 1

HCID 681816251-(2-Aminopyrimidin-4-yl)-6-bromoindazole-3-carboxamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 1-(2-aminopyrimidin-4-yl)-6-bromoindazole-3-carboxylic acid (500 mg, 1.32 mmol) in DCM (5 mL), was added thionyl chloride (0.6 mL, 7.9 mmol) followed by DMF (0.02 mL). The mixture was stirred at RT for 1 hr. The mixture was concentrated in vacuo, DCM (2 mL) added and concentration in vacuo was repeated. To this residue was added THF (5 mL) and conc. aq NH3 (0.5 mL). The mixture stirred for 30 min, then diluted with water and the resultant solid was collected by suction filtration. The solid was thoroughly dried under high vacuum, to give the title compound (360 mg): 1H NMR (250 MHz, DMSO) delta 7.15 (1H, br. s.), 7.32 (1H, d, J=5.48 Hz), 7.60 (1H, dd, J=8.60, 1.60 Hz), 7.74 (1H, br. s.), 8.20 (1H, d, J=8.38 Hz), 8.38 (1H, d, J=5.48 Hz), 9.18 (1H, d, J=1.22 Hz); LC-MS: m/z=+332.90/334.70 (M+H)+.

후처리

  1. concentrationThe mixture was concentrated in vacuo, DCM (2 mL)
  2. additionadded
  3. concentrationconcentration in vacuo
  4. additionTo this residue was added THF (5 mL) and conc. aq NH3 (0.5 mL)
  5. stirringThe mixture stirred for 30 min
  6. additiondiluted with water
  7. filtrationthe resultant solid was collected by suction filtration
  8. customThe solid was thoroughly dried under high vacuum

출처 및 근거

ORD 기록
ord-4991ad4935c94f43aa411df6a445dba3
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901313B2

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