Triphenylphosphine → 4-(6-Chlorobenzofuran-7-ylamino)-6-methoxy-7-(2-pyrrolidin-1-ylethoxy)quinazoline

HRID 22782

반응식

HRID 22782 반응식
N(C(OCC)=O)=NC(OCC)=O.[Cl:13][C:14]1[CH:22]=[CH:21][C:17]2[CH:18]=[CH:19][O:20][C:16]=2[C:15]=1[NH:23][C:24]1[C:33]2[C:28](=[CH:29][C:30]([OH:36])=[C:31]([O:34][CH3:35])[CH:32]=2)[N:27]=[CH:26][N:25]=1.O[CH2:38][CH2:39][N:40]1[CH2:44][CH2:43][CH2:42][CH2:41]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Cl:13][C:14]1[CH:22]=[CH:21][C:17]2[CH:18]=[CH:19][O:20][C:16]=2[C:15]=1[NH:23][C:24]1[C:33]2[C:28](=[CH:29][C:30]([O:36][CH2:38][CH2:39][N:40]3[CH2:44][CH2:43][CH2:42][CH2:41]3)=[C:31]([O:34][CH3:35])[CH:32]=2)[N:27]=[CH:26][N:25]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 762881-PyrrolidineethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 1357330214-(6-Chlorobenzofuran-7-ylamino)-7-hydroxy-6-methoxyquinazoline

생성물 1

HCID 102251714-(6-Chlorobenzofuran-7-ylamino)-6-methoxy-7-(2-pyrrolidin-1-ylethoxy)quinazoline수율 25.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Diethyl azodicarboxylate (0.101 ml) was added dropwise to a stirred mixture of 4-(6-chlorobenzofuran-7-ylamino)-7-hydroxy-6-methoxyquinazoline (0.1 g), 1-(2-hydroxyethyl)pyrrolidine (0.04 g), triphenylphosphine (0.169 g) and methylene chloride (5 ml) and the reaction mixture was stirred at ambient temperature for 2 hours. The solvent was evaporated and the residue was purified by column chromatography on silica using increasingly polar mixture of methylene chloride and a saturated methanolic ammonia solution as eluent. There was thus obtained the title compound (0.033 g) as a solid; NMR Spectrum: (DMSOd6 and CF3CO2D) 1.9 (m, 2H), 2.1 (m, 2H), 3.2 (m, 2H), 3.65-3.85 (m, 4H), 4.05 (s, 3H), 4.6 (m, 2H), 7.15 (d, 1H), 7.45 (s, 1H), 7.6 (d, 1H), 7.8 (d, 1H), 8.1 (d, 1H), 8.25 (s, 1H), 8.85 (s, 1H); Mass Spectrum: M+H+ 439.

후처리

  1. customThe solvent was evaporated
  2. customthe residue was purified by column chromatography on silica using
  3. temperatureincreasingly polar
  4. additionmixture of methylene chloride

출처 및 근거

ORD 기록
ord-5775e14afd58470c9edbd4621bc817c6
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06849625B2

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