Water → 4-(4-chloro-6-(5-isopropyl-2-methylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)-3,5-dimethyl-1H-indazole-1-carbaldehyde

HRID 80851

반응식

HRID 80851 반응식
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH3:32])[C:9]=2[C:11]2[N:12]=[C:13](O)[C:14]3[CH2:20][N:19]([C:21]4[CH:26]=[C:25]([CH:27]([CH3:29])[CH3:28])[CH:24]=[CH:23][C:22]=4[CH3:30])[CH2:18][CH2:17][C:15]=3[N:16]=2)[NH:4][N:3]=1.[CH3:33][N+](C)=C[Cl:36].[Cl-:38].[OH2:39]>ClCCCl>[Cl:36][C:13]1[C:14]2[CH2:20][N:19]([C:21]3[CH:26]=[C:25]([CH:27]([CH3:29])[CH3:28])[CH:24]=[CH:23][C:22]=3[CH3:30])[CH2:18][CH2:17][C:15]=2[N:16]=[C:11]([C:9]2[C:8]([CH3:32])=[CH:7][CH:6]=[C:5]3[C:10]=2[C:2]([CH3:1])=[N:3][NH:4]3)[N:12]=1.[Cl:38][C:13]1[C:14]2[CH2:20][N:19]([C:21]3[CH:26]=[C:25]([CH:27]([CH3:28])[CH3:29])[CH:24]=[CH:23][C:22]=3[CH3:30])[CH2:18][CH2:17][C:15]=2[N:16]=[C:11]([C:9]2[C:8]([CH3:32])=[CH:7][CH:6]=[C:5]3[C:10]=2[C:2]([CH3:1])=[N:3][N:4]3[CH:33]=[O:39])[N:12]=1

참가 물질

6

반응물 3

HCID 962WaterHCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 178424912HCID 178424912, 화합물

생성물 2

HCID 866902884-(4-chloro-6-(5-isopropyl-2-methylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)-3,5-dimethyl-1H-indazole-1-carbaldehydeHCID 178424910HCID 178424910, 화합물

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

반응 조건

온도
50 °C

실험 절차

To a suspension of 2-(3,5-dimethyl-1H-indazol-4-yl)-6-(5-isopropyl-2-methylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-ol (1.3 g, 3.04 mmol) in DCE (50 mL) was added Vilsmeier reagent (1.95 g, 15.2 mmol). The mixture was heated at 50° C. for 2 h. LC-MS showed reaction complete. The reaction mixture was poured into water, and the layers were separated. The aqueous layer was extracted with DCM. The organics were combined and concentrated. The residue was purified by FCC (0-100% EtOAc/heptane) to provide 4-chloro-2-(3,5-dimethyl-1H-indazol-4-yl)-6-(5-isopropyl-2-methylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine MS (ESI+) m/z 446.3 (M+H)+ and 4-(4-chloro-6-(5-isopropyl-2-methylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)-3,5-dimethyl-1H-indazole-1-carbaldehyde MS (ESE) m/z 474.3 (M+H)+.

후처리

  1. customreaction complete
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with DCM
  4. concentrationconcentrated
  5. customThe residue was purified by FCC (0-100% EtOAc/heptane)

출처 및 근거

ORD 기록
ord-cd341f6566c64530a0ac3e7817106fd5
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846656B2

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