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

反応式

HRID 80851 の反応式
[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

参加物

6

反応物 3

HCID 962WaterHCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 178424912HCID 178424912、化合物

生成物 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、化合物

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

反応条件

温度
50 °C

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-cd341f6566c64530a0ac3e7817106fd5
出典データセット
uspto-grants-2014_09
特許番号
US08846656B2

関連ノート

読み込み中…