3-Dimethylaminobenzoyl chloride → 4-[2-Methyl-5-(3-dimethylaminobenzamido)anilino]-6,7,8-trimethoxyquinazoline

HRID 2084005

반응식

HRID 2084005 반응식
[CH3:1][N:2]([CH3:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].[CH3:13][C:14]1[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][C:15]=1[NH:16][C:17]1[C:26]2[C:21](=[C:22]([O:31][CH3:32])[C:23]([O:29][CH3:30])=[C:24]([O:27][CH3:28])[CH:25]=2)[N:20]=[CH:19][N:18]=1>C(Cl)Cl>[CH3:13][C:14]1[CH:36]=[CH:35][C:34]([NH:37][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][CH:11]=[C:3]([N:2]([CH3:12])[CH3:1])[CH:4]=2)=[CH:33][C:15]=1[NH:16][C:17]1[C:26]2[C:21](=[C:22]([O:31][CH3:32])[C:23]([O:29][CH3:30])=[C:24]([O:27][CH3:28])[CH:25]=2)[N:20]=[CH:19][N:18]=1

참가 물질

4

반응물 2

HCID 70103423-Dimethylaminobenzoyl chlorideHCID 227322614-(2-Methyl-5-aminoanilino)-6,7,8-trimethoxyquinazoline

생성물 1

HCID 227322894-[2-Methyl-5-(3-dimethylaminobenzamido)anilino]-6,7,8-trimethoxyquinazoline수율 12%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

3-Dimethylaminobenzoyl chloride (105 mg) was added to a suspension of 4-(2-methyl-5-aminoanilino)-6,7,8-trimethoxyquinazoline (180 mg) in dry methylene chloride (4 ml) and the resulting mixture was stirred at ambient temperature for 18 hours. Methylene chloride (100 ml) was added and the mixture washed with aqueous sodium hydroxide solution (100 ml), water and brine, dried over sodium sulphate, filtered and evaporated give a yellow gum. This was purified by silica column chromatography, eluting with 2% methanol in methylene chloride to yield the title compound as a solid (30 mg, 12%); NMR (CDCl3) 2.22 (s, 3H), 2.97 (s, 6H), 3.96 (s, 3H), 4.06 (s, 3H), 4.13 (s, 3H), 6.84 (dd, 1H), 7.05 (m, 2H), 7.18 (m, 2H), 7.28 (t, 1H), 7.42 (m, 1H), 7.92 (s, 1H), 7.95 (s, 1H), 8.61 (s, 1H); m/s: M+H+ 488.

후처리

  1. washthe mixture washed with aqueous sodium hydroxide solution (100 ml), water and brine
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. customgive a yellow gum
  6. customThis was purified by silica column chromatography
  7. washeluting with 2% methanol in methylene chloride

출처 및 근거

ORD 기록
ord-3500dcb2c4c5456b899bc320995202fe
출처 데이터셋
uspto-grants-2004_04
특허 번호
US06716847B2

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