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

HRID 641779

반응식

HRID 641779 반응식
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

참가 물질

9

반응물 5

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

생성물 1

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

시약·촉매·용매 3

HCID 702Ethanol용매HCID 3283Diethyl Ether용매2회HCID 6344Dichloromethane용매3회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a5e062647a6b494d9ae853990f02bf44
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696214B2

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