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Methane, dichloromethoxy- → 5-(6-Phenyl-thieno[3,2-d]pyrimidin-4-ylamino)-1H-indole-3-carbaldehyde

HRID 2297814
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HRID 2297814 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11]3[C:12]4[S:19][C:18]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)=[CH:17][C:13]=4[N:14]=[CH:15][N:16]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Cl[CH:27](Cl)[O:28]C>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[C:20]1([C:18]2[S:19][C:12]3[C:11]([NH:10][C:6]4[CH:5]=[C:4]5[C:9](=[CH:8][CH:7]=4)[NH:1][CH:2]=[C:3]5[CH:27]=[O:28])=[N:16][CH:15]=[N:14][C:13]=3[CH:17]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1
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참가 물질

5

반응물 2

HCID 21004Methane, dichloromethoxy-HCID 9884465(1H-Indol-5-yl)-(6-phenyl-thieno[3,2-d]pyrimidin-4-yl)-amine

생성물 1

HCID 183827505-(6-Phenyl-thieno[3,2-d]pyrimidin-4-ylamino)-1H-indole-3-carbaldehyde수율 92%

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of (1H-Indol-5-yl)-(6-phenyl-thieno[3,2-d]pyrimidin-4-yl)-amine (481 mg, 1.4 mmol) in 3 mL of methylene chloride in a 3-neck flask with dropping funnel under nitrogen at 0° C. was added titanium tetrachloride (461 mL, 4.2 mmol) dropwise. The mixture was stirred for 30 minutes and then dichloromethoxy methane (380 mL, 4.2 mmol) was added dropwise. The reaction was warmed to room temperature and concentrated in vacuo. The resulting residue was pre-absorbed onto silica gel (10 gm) and purified by flash chromatography using a 5% methanol/methylene chloride to afford the title compound in 92% yield. RP18-HPLC RT: 4.80 minutes; API MS: 371.20 (M+1); MP: 174-175° C.

후처리

  1. concentrationconcentrated in vacuo
  2. customThe resulting residue was pre-absorbed onto silica gel (10 gm)
  3. custompurified by flash chromatography

출처 및 근거

ORD 기록
ord-6a287ddceffc4e7ea6c12046521ca186
출처 데이터셋
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06492383B1

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