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Ethanol → 4-(2-Chloro-5-methoxyanilino)-7-hydroxy-5-(3-morpholinopropoxy)quinazoline

HRID 641727
노트
인쇄 미리보기

반응식

HRID 641727 반응식
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:19][C:20]3[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=3[Cl:28])=[N:14][CH:15]=[N:16]2)=[C:11]([O:29][CH2:30][CH2:31][CH2:32][N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)[CH:10]=1)C1C=CC=CC=1.C(O)C.C1COCC1.[H][H]>[Pd].CN(C=O)C>[Cl:28][C:21]1[CH:22]=[CH:23][C:24]([O:26][CH3:27])=[CH:25][C:20]=1[NH:19][C:13]1[C:12]2[C:17](=[CH:18][C:9]([OH:8])=[CH:10][C:11]=2[O:29][CH2:30][CH2:31][CH2:32][N:33]2[CH2:34][CH2:35][O:36][CH2:37][CH2:38]2)[N:16]=[CH:15][N:14]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 221408327-Benzyloxy4-(2-chloro-5-methoxyanilino)-5-(3-morpholinopropoxy)quinazolineHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 1358309164-(2-Chloro-5-methoxyanilino)-7-hydroxy-5-(3-morpholinopropoxy)quinazoline수율 29.3%

시약·촉매·용매 2

HCID 23938
Palladium
촉매
HCID 6228Dimethylformamide용매

실험 절차

A mixture of 7-benzyloxy-4-(2-chloro-5-methoxyanilino)-5-(3-morpholinopropoxy)quinazoline (0.185 g), 10% palladium on charcoal catalyst (0.018 g), ethanol (2.5 ml), THF (2.5 ml) and DMF (1 ml) was stirred under an atmosphere pressure of hydrogen for 16 hours. The mixture was filtered and the filtrate was evaporated. The residue was purified by column chromatography on silica using a 9:1 mixture of methylene chloride and a saturated methanolic ammonia solution as eluent. There was thus obtained the title compound (0.045 g); NMR Spectrum: (DMSOd6) 2.05 (m, 2H), 2.35 (br s, 4H), 2.45 (t, 2H), 3.55 (t, 4H), 3.8 (s, 3H), 4.42 (t, 2H), 6.7 (d, 2H), 7.45 (d, 1H), 8.3 (s, 1H), 8.45 (s, 1H), 10.05 (s, 1H); Mass Spectrum: M+H+ 445.

후처리

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column chromatography on silica using
  4. additiona 9:1 mixture of methylene chloride

출처 및 근거

ORD 기록
ord-e7ecbd9558c64f79810f95b8a9e8ff9b
출처 데이터셋
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07696214B2

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