p-Toluenesulfonic acid → 2-(4-(1-Acetylpiperidin-4-yloxy)phenyl)-5,7-dimethoxyquinazolin-4(3H)-one

HRID 591711노트

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HRID 591711 반응식
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([O:13][CH3:14])[C:3]=1[C:4]([NH2:6])=[O:5].[C:15]([N:18]1[CH2:23][CH2:22][CH:21]([O:24][C:25]2[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=2)[CH2:20][CH2:19]1)(=[O:17])[CH3:16].OS([O-])=O.[Na+].CC1C=CC(S(O)(=O)=O)=CC=1>CN(C)C(=O)C>[C:15]([N:18]1[CH2:23][CH2:22][CH:21]([O:24][C:25]2[CH:26]=[CH:27][C:28]([C:29]3[NH:6][C:4](=[O:5])[C:3]4[C:2](=[CH:10][C:9]([O:11][CH3:12])=[CH:8][C:7]=4[O:13][CH3:14])[N:1]=3)=[CH:31][CH:32]=2)[CH2:20][CH2:19]1)(=[O:17])[CH3:16]

참가 물질

6

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 203490162-Amino-4,6-dimethoxybenzamideHCID 230875244-(1-Acetylpiperidin-4-yloxy)benzaldehydeHCID 23665763Sodium Bisulfite

생성물 1

HCID 1359390502-(4-(1-Acetylpiperidin-4-yloxy)phenyl)-5,7-dimethoxyquinazolin-4(3H)-one

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

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온도
115 °C

실험 절차

To a solution of 2-amino-4,6-dimethoxy-benzamide (0.20 g, 1.0 mmol) and 4-(1-acetyl-piperidin-4-yloxy)-benzaldehyde (0.25 g, 1.0 mmol) in N,N-dimethyl acetamide (5 mL), NaHSO3 (0.20 g, 1.1 mmol) and p-TSA (20 mg, 0.10 mmol) were added and the reaction mixture was heated at 115° C. for 16 hours. The reaction mixture was cooled to room temperature. N,N-dimethylacetamide was removed under reduced pressure. The residue was diluted with water and the solid was collected; the crude product was purified by column chromatography on silica gel (230-400 mesh), using 5% methanol in CH2Cl2 as eluent, to give the title compound. Yield: 0.2 g (47%). MP 275-277° C. 1H NMR (400 Hz, CDCl3): δ 11.94 (s, 1H), 8.16 (d, 2H), 7.10 (d, 2H), 6.70 (d, 1H), 6.50 (d, 1H), 4.76 (m, 1H), 3.88 (s, 3H), 3.82 (s, 3H), 3.70 (m, 1H), 3.30 (m, 2H), 3.20 (m, 1H), 2.04 (s, 3H), 1.95 (m, 2H), 1.64 (m, 1H), 1.52 (m, 1H).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customN,N-dimethylacetamide was removed under reduced pressure
  3. additionThe residue was diluted with water
  4. customthe solid was collected
  5. customthe crude product was purified by column chromatography on silica gel (230-400 mesh)

출처 및 근거

ORD 기록
ord-d32aacb8eb73419bba1aec23bae6cdd8
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238640B2

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