Methanol → N-(3-(1H-pyrazolo[3,4-d]pyrimidin-4-yl)pyridin-2-yl)-1-chloro-6-methylisoquinolin-5-amine

HRID 1042290

반응식

HRID 1042290 반응식
[Cl:1][C:2]1[C:11]2[CH:10]=[CH:9][C:8]([CH3:12])=[C:7]([NH2:13])[C:6]=2[CH:5]=[CH:4][N:3]=1.F[C:15]1[C:20]([C:21]2[N:26]=[CH:25][N:24]=[C:23]3[NH:27][N:28]=[CH:29][C:22]=23)=[CH:19][CH:18]=[CH:17][N:16]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].CO>C1COCC1.CC(O)=O>[NH:27]1[C:23]2=[N:24][CH:25]=[N:26][C:21]([C:20]3[C:15]([NH:13][C:7]4[C:6]5[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[C:11]=5[CH:10]=[CH:9][C:8]=4[CH3:12])=[N:16][CH:17]=[CH:18][CH:19]=3)=[C:22]2[CH:29]=[N:28]1

참가 물질

7

반응물 4

HCID 887MethanolHCID 2733832Lithium HexamethyldisilazideHCID 596273751-Chloro-6-methylisoquinolin-5-amineHCID 596273834-(2-fluoropyridin-3-yl)-1H-pyrazolo[3,4-d]pyrimidine

생성물 1

HCID 59627378N-(3-(1H-pyrazolo[3,4-d]pyrimidin-4-yl)pyridin-2-yl)-1-chloro-6-methylisoquinolin-5-amine

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 8028Tetrahydrofuran용매2회

실험 절차

A mixture of 1-chloro-6-methylisoquinolin-5-amine (414 mg, 2147 μmol) and 4-(2-fluoropyridin-3-yl)-1H-pyrazolo[3,4-d]pyrimidine (420 mg, 1952 μmol) in THF (20 ml) was sonicated until all solid became a fine powder. Lithium bis(trimethylsilyl)amide, 1.0 M solution in THF (6831 μl, 6831 mmol) was then added (all solids were dissolved and color changed) The mixture was stirred at rt overnight. The mixture was poured into a mixture of MeOH (20 ml) and AcOH (2 ml) and then solvent was removed in vacuo. 2 M NH3/MeOH (30 ml) was added and then solvent was removed in vacuo. The product was purified by flash chromatography eluting with MeOH/DCM (0-5%) to give N-(3-(1H-pyrazolo[3,4-d]pyrimidin-4-yl)pyridin-2-yl)-1-chloro-6-methylisoquinolin-5-amine. MS Found (ESI pos. ion) m/z 388 (M+H+).

후처리

  1. customwas sonicated until all solid
  2. dissolutionwere dissolved
  3. customsolvent was removed in vacuo
  4. addition2 M NH3/MeOH (30 ml) was added
  5. customsolvent was removed in vacuo
  6. customThe product was purified by flash chromatography
  7. washeluting with MeOH/DCM (0-5%)

출처 및 근거

ORD 기록
ord-118208ef04274e5680c3c4c71d6071e0
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557830B2

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