Triphenylphosphine → 4-(2-Chloro-5-methoxyanilino)-5,7-di-(3-morpholinopropoxy)quinazoline

HRID 1373281

반응식

HRID 1373281 반응식
N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.[Cl:17][C:18]1[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][C:19]=1[NH:20][C:21]1[C:30]2[C:25](=[CH:26][C:27]([OH:41])=[CH:28][C:29]=2[O:31][CH2:32][CH2:33][CH2:34][N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)[N:24]=[CH:23][N:22]=1.O[CH2:49][CH2:50][CH2:51][N:52]1[CH2:57][CH2:56][O:55][CH2:54][CH2:53]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Cl:17][C:18]1[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][C:19]=1[NH:20][C:21]1[C:30]2[C:25](=[CH:26][C:27]([O:41][CH2:49][CH2:50][CH2:51][N:52]3[CH2:57][CH2:56][O:55][CH2:54][CH2:53]3)=[CH:28][C:29]=2[O:31][CH2:32][CH2:33][CH2:34][N:35]2[CH2:36][CH2:37][O:38][CH2:39][CH2:40]2)[N:24]=[CH:23][N:22]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 1995763-Morpholino-1-propanolHCID 1358309164-(2-Chloro-5-methoxyanilino)-7-hydroxy-5-(3-morpholinopropoxy)quinazoline

생성물 1

HCID 98728724-(2-Chloro-5-methoxyanilino)-5,7-di-(3-morpholinopropoxy)quinazoline수율 31.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Di-tert-butyl azodicarboxylate (0.035 g) was added dropwise to a stirred mixture of 4-(2-chloro-5-methoxyanilino)-7-hydroxy-5-(3-morpholinopropoxy)quinazoline (0.045 g), 4-(3-hydroxypropyl)morpholine (0.016 g), triphenylphosphine (0.04 g) and methylene chloride (1 ml). The reaction mixture was stirred at ambient temperature for 10 minutes. The mixture was evaporated and the residue was purified by column chromatography on silica using a 9:10:1 mixture of methylene chloride, ethyl acetate and a saturated methanolic ammonia solution as eluent. The material so obtained was triturated under diethyl ether. The resultant solid was isolated, washed with diethyl ether and dried under vacuum to give the title compound (0.018 g); NMR Spectrum: DMSOd6 and CF3COOD) 2.2–2.4 (m, 4H), 3.15 (m, 4H), 3.35 (m, 4H), 3.5 (m, 4H), 3.7 (m, 4H), 3.8 (s, 3H), 4.02 (t, 4H), 4.35 (t, 2H), 4.6 (t, 2H), 6.95 (s, 1H), 7.03 (s, 1H), 7.05 (m, 1H), 7.5 (s, 1H), 7.6 (d, 1H), 8.88 (s, 1H); Mass Spectrum: M+H+ 572 and 574.

후처리

  1. customThe mixture was evaporated
  2. customthe residue was purified by column chromatography on silica using
  3. additiona 9:10:1 mixture of methylene chloride, ethyl acetate
  4. customThe material so obtained
  5. customwas triturated under diethyl ether
  6. customThe resultant solid was isolated
  7. washwashed with diethyl ether
  8. customdried under vacuum

출처 및 근거

ORD 기록
ord-b0004c407c4843788b682da8ae6afe18
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07160891B2

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