Ammonia → 4-(6-Chloro-2,3-methylenedioxyanilino)-7-ethoxy-5-(1-methylpiperidin-4-yloxy)quinazoline

HRID 641779

反応式

HRID 641779 の反応式
N(C(O[C:9](C)(C)[CH3:10])=O)=NC([O-])=O.[Cl:13][C:14]1[C:19]([NH:20][C:21]2[C:30]3[C:25](=[CH:26][C:27]([OH:39])=[CH:28][C:29]=3[O:31][CH:32]3[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]3)[N:24]=[CH:23][N:22]=2)=[C:18]2[O:40][CH2:41][O:42][C:17]2=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl.N>C(Cl)Cl.C(OCC)C.C(O)C>[Cl:13][C:14]1[C:19]([NH:20][C:21]2[C:30]3[C:25](=[CH:26][C:27]([O:39][CH2:9][CH3:10])=[CH:28][C:29]=3[O:31][CH:32]3[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]3)[N:24]=[CH:23][N:22]=2)=[C:18]2[O:40][CH2:41][O:42][C:17]2=[CH:16][CH:15]=1

参加物

9

反応物 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 86609045Tert-butyl azodicarboxylateHCID 1355107014-(6-chloro-2,3-methylenedioxyanilino)-7-hydroxy-5-(N-methylpiperidin-4-yloxy)quinazoline

生成物 1

HCID 685792644-(6-Chloro-2,3-methylenedioxyanilino)-7-ethoxy-5-(1-methylpiperidin-4-yloxy)quinazoline収率 72%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 3283Diethyl Ether溶媒2 回HCID 6344Dichloromethane溶媒3 回

実験手順

A solution of di-(tert-butyl azodicarboxylate (0.26 g) in methylene chloride (1 ml) was added dropwise to a stirred mixture of 4-(6-chloro-2,3-methylenedioxyanilino)-7-hydroxy-5-(N-methylpiperidin-4-yloxy)quinazoline (0.12 g), ethanol (0.019 g), triphenylphosphine (0.15 g) and methylene chloride (2 ml) and the resultant mixture was stirred at ambient temperature for 1 hour. A 2M solution of hydrogen chloride in diethyl ether (3 ml) was added and the mixture was stirred at ambient temperature for 1.5 hours. Diethyl ether (1 ml) was added and the precipitate was isolated and dried under vacuum. The solid so obtained was dissolved in a 9:1 mixture of methylene chloride and a saturated methanolic ammonia solution. The mixture was filtered and the filtrate was evaporated. The residue was triturated under pentane and the resultant solid was isolated and dried under vacuum. There was thus obtained the title compound (0.092 g); NMR Spectrum: (CDCl3) 1.5 (t, 3H), 1.95-2.1 (m, 2H), 2.15-2.5 (m, 2H), 2.3 (s, 3H), 2.3-2.4 (m, 2H), 2.7 (br s, 2H), 4.15 (m, 2H), 4.6 (m, 1H), 6.05 (s, 2H), 6.5 (d, 1H), 6.7 (d, 1H), 6.8 (d, 1H), 6.95 (d, 1H), 8.5 (s, 1H), 9.25 (br s, 1H); Mass Spectrum: M+H+ 457 and 459.

後処理

  1. customthe precipitate was isolated
  2. customdried under vacuum
  3. customThe solid so obtained
  4. filtrationThe mixture was filtered
  5. customthe filtrate was evaporated
  6. customThe residue was triturated under pentane
  7. customthe resultant solid was isolated
  8. customdried under vacuum

出典と根拠

ORDレコード
ord-a5e062647a6b494d9ae853990f02bf44
出典データセット
uspto-grants-2010_04
特許番号
US07696214B2

関連ノート

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