Triphenylphosphine → 4-(2-Methylindol-5-yloxy)-7-(3-(pyrrolidin-yl)propoxy)quinazoline

HRID 454083

반응식

HRID 454083 반응식
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[OH:15][C:16]1[CH:25]=[C:24]2[C:19]([C:20]([O:26][C:27]3[CH:28]=[C:29]4[C:33](=[CH:34][CH:35]=3)[NH:32][C:31]([CH3:36])=[CH:30]4)=[N:21][CH:22]=[N:23]2)=[CH:18][CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:56]1([CH2:61][CH2:62][CH2:63]O)[CH2:60][CH2:59][CH2:58][CH2:57]1>C(Cl)Cl>[CH3:36][C:31]1[NH:32][C:33]2[C:29]([CH:30]=1)=[CH:28][C:27]([O:26][C:20]1[C:19]3[C:24](=[CH:25][C:16]([O:15][CH2:63][CH2:62][CH2:61][N:56]4[CH2:60][CH2:59][CH2:58][CH2:57]4)=[CH:17][CH:18]=3)[N:23]=[CH:22][N:21]=1)=[CH:35][CH:34]=2

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 2093421-PyrrolidinepropanolHCID 1357631147-Hydroxy-4-(2-methylindol-5-yloxy)quinazoline

생성물 1

HCID 220308234-(2-Methylindol-5-yloxy)-7-(3-(pyrrolidin-yl)propoxy)quinazoline수율 35.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Diisopropyl azodicarboxylate (146 mg, 0.72 mmol) was added to a solution of 7-hydroxy-4-(2-methylindol-5-yloxy)quinazoline (100 mg, 0.34 mmol), triphenyl phosphine (189 mg, 0.72 mol), and 3-pyrrolidinopropan-1-ol (89 mg, 0.686 mmol), (J. Org. Chem. 1988, 53, 3164), in methylene chloride (2.5 ml). After stirring overnight at ambient temperature, the solid was filtered. The filtrate was purified by column chromatography eluting with ethyl acetate/methylene chloride (1/1) followed by ethyl acetate/methylene chloride/methanol (4/5/1), methylene chloride/methanol (9/1) and 3N ammonia in methanol/methylene chloride (1/9). After removal of the solvent, the residue was triturated with ether, filtered, and dried under vacuum to give 4-(2-methylindol-5-yloxy)-7-(3-(pyrrolidin-yl)propoxy)quinazoline (49 mg, 35%).

후처리

  1. filtrationthe solid was filtered
  2. customThe filtrate was purified by column chromatography
  3. washeluting with ethyl acetate/methylene chloride (1/1)
  4. customAfter removal of the solvent
  5. customthe residue was triturated with ether
  6. filtrationfiltered
  7. customdried under vacuum

출처 및 근거

ORD 기록
ord-e98edf82ec354b419fca0bd04427b408
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492560B2

연결된 노트

불러오는 중…