Dimethylformamide → [4-(Benzyloxy)-5-methoxy-2-nitrophenyl][4-(4-quinazolinyl)piperazino]methanone

HRID 1876823노트

반응식

HRID 1876823 반응식
CN(C=O)C.[C:6]([O:14][C:15]1[C:23]([O:24][CH3:25])=[CH:22][C:18]([C:19]([OH:21])=O)=[C:17]([N+:26]([O-:28])=[O:27])[CH:16]=1)(=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.S(Cl)(Cl)=O.[N:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:36]([N:43]2[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]2)=[N:35][CH:34]=1>C1C=CC=CC=1>[CH2:6]([O:14][C:15]1[C:23]([O:24][CH3:25])=[CH:22][C:18]([C:19]([N:46]2[CH2:47][CH2:48][N:43]([C:36]3[C:37]4[C:42](=[CH:41][CH:40]=[CH:39][CH:38]=4)[N:33]=[CH:34][N:35]=3)[CH2:44][CH2:45]2)=[O:21])=[C:17]([N+:26]([O-:28])=[O:27])[CH:16]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 18585334-Piperazin-1-ylquinazolineHCID 594400844-Benzoyloxy-5-methoxy-2-nitro benzoic acid

생성물 1

HCID 66882459[4-(Benzyloxy)-5-methoxy-2-nitrophenyl][4-(4-quinazolinyl)piperazino]methanone수율 84%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

DMF was added to a stirred suspension of 4-benzoyloxy-5-methoxy-2-nitro benzoic acid (6) (0:500 mg, 1.65 mmol) and thionyl chloride (3 ml) in dry benzene (30 ml) and the stirring was continued for 6 h. The benzene was evaporated in vacuum and the resultant oil dissolved in dry THF (50 ml) and added dropwise over a period of 1 h to a stirred suspension of (4-quinazolinyl)piperazine (350 mg, 1.65 mmol) triethyl amine (5 ml). After the completion of addition, the reaction mixture was brought to ambient temperature and stirred for an additional hour. The THF was evaporated in vacuum and the aqueous layer was washed with ethyl acetate. The aqueous phase was then adjusted to pH 3 using 6 N HCl and extracted with ethyl acetate and washed with brine, dried over Na2SO4 and evaporated in vacuum to afford the crude product of (7d), (700 mg in 84% yield). 1H NMR (CDCl3) δ 3.15-3.30 (m, 4H), 3.65-3.75 (m, 4H), 3.95 (s, 3H), 5.20 (s, 2H), 6.45-6.55 (t, 1H) 6.70 (s, 1H), 7.30-7.50 (m, 5H), 7.55-7.65 (t, 1H), 7.65 (s, 1H), 7.70-7.90 (m, 2H), 7.85-7.95 (m, 2H); FABMS: 500 (M+H)+.

후처리

  1. customThe benzene was evaporated in vacuum
  2. dissolutionthe resultant oil dissolved in dry THF (50 ml)
  3. additionAfter the completion of addition
  4. customwas brought to ambient temperature
  5. customThe THF was evaporated in vacuum
  6. washthe aqueous layer was washed with ethyl acetate
  7. extractionextracted with ethyl acetate
  8. washwashed with brine
  9. dry with materialdried over Na2SO4
  10. customevaporated in vacuum

출처 및 근거

ORD 기록
ord-fa095f970c4540d4bbfa1d41e0941ca7
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08309726B2

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