p-Toluenesulfonic acid → 2-(4-(4-Isopropylpiperazin-1-yl)phenyl)-8-methoxyquinazolin-4(3H)-one

HRID 591651노트

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HRID 591651 반응식
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].OS([O-])=O.[Na+].CC1C=CC(S(O)(=O)=O)=CC=1.[NH2:34][C:35]1[C:43]([O:44][CH3:45])=[CH:42][CH:41]=[CH:40][C:36]=1[C:37]([NH2:39])=[O:38]>CC(N(C)C)=O.O.C([O-])(O)=O.[Na+]>[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:17]=[CH:16][C:13]([C:14]3[NH:39][C:37](=[O:38])[C:36]4[C:35](=[C:43]([O:44][CH3:45])[CH:42]=[CH:41][CH:40]=4)[N:34]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

참가 물질

8

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 20522144-(4-Isopropylpiperazin-1-yl)benzaldehydeHCID 185365712-Amino-3-methoxybenzamideHCID 23665763Sodium Bisulfite

생성물 1

HCID 1359391202-(4-(4-Isopropylpiperazin-1-yl)phenyl)-8-methoxyquinazolin-4(3H)-one수율 15.4%

시약·촉매·용매 3

HCID 962Water용매HCID 31374Dimethylacetamide용매HCID 516892Sodium Bicarbonate용매

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온도
120 °C

실험 절차

A mixture of 4-(4-isopropylpiperazin-1-yl)benzaldehyde (0.562 g, 2.40 mmol), NaHSO3 (0.310 g, 2.90 mmol), and p-TsOH (0.046 g, 0.24 mmol) was added to a solution of 2-amino-3-methoxybenzamide (0.400 g, 2.40 mmol) in DMA (15 mL). The reaction was stirred at 120° C. overnight. The mixture was diluted with H2O and saturated NaHCO3 and extracted with CH2Cl2. The organics were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel eluting with 0% to 10% MeOH/CH2Cl2 afforded the title compound (0.140 g, 15%). 1H NMR (300 MHz, DMSO-d6): δ 12.27 (s, 1H), 8.10 (d, J=8.9 Hz, 2H), 7.64-7.70 (m, 1H), 7.31-7.39 (m, 2H), 7.03 (d, J=9.1 Hz, 2H), 3.93 (s, 3H), 3.27-3.32 (m, 4H), 2.64-2.75 (m, 1H), 2.56-2.59 (m, 4H), 1.00 (d, J=6.6 Hz, 6H). ESI MS m/z 379 [M+H]+.

후처리

  1. extractionextracted with CH2Cl2
  2. washThe organics were washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel eluting with 0% to 10% MeOH/CH2Cl2

출처 및 근거

ORD 기록
ord-6e0a8c79472a44e3bd3b2a802f527031
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238640B2

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