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

HRID 1373281

反応式

HRID 1373281 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b0004c407c4843788b682da8ae6afe18
出典データセット
uspto-grants-2007_01
特許番号
US07160891B2

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