p-Toluenesulfonic acid monohydrate → 2-(2-(2-Hydroxyethyl)-1H-indol-5-yl)-5,7-dimethoxyquinazolin-4(3H)-one

HRID 591682노트

반응식

HRID 591682 반응식
[OH:1][CH2:2][CH2:3][C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([CH:13]=O)=[CH:8][CH:7]=2.[NH2:15][C:16]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([O:27][CH3:28])[C:17]=1[C:18]([NH2:20])=[O:19].S([O-])(O)=O.[Na+].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C)C(=O)C>[OH:1][CH2:2][CH2:3][C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([C:13]1[NH:20][C:18](=[O:19])[C:17]3[C:16](=[CH:24][C:23]([O:25][CH3:26])=[CH:22][C:21]=3[O:27][CH3:28])[N:15]=1)=[CH:8][CH:7]=2

참가 물질

6

반응물 4

HCID 521998p-Toluenesulfonic acid monohydrateHCID 203490162-Amino-4,6-dimethoxybenzamideHCID 23665763Sodium BisulfiteHCID 866620292-(2-hydroxy-ethyl)-1H-indole-5-carbaldehyde

생성물 1

HCID 1359390342-(2-(2-Hydroxyethyl)-1H-indol-5-yl)-5,7-dimethoxyquinazolin-4(3H)-one

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

반응 조건

온도
120 °C

실험 절차

To a solution of 2-(2-hydroxy-ethyl)-1H-indole-5-carbaldehyde (0.300 g, 1.58 mmol) and 2-amino-4,6-dimethoxy-benzamide (0.370 g, 1.90 mmol) in N,N-dimethylacetamide (5 mL) were added sodium hydrogen sulfite (58.5 wt %) (0.350 g, 1.90 mmol) and p-toluenesulfonic acid monohydrate (60 mg, 0.32 mmol). The reaction mixture was stirred at 120° C. for 16 hours under nitrogen and cooled to room temperature. The solvent was evaporated under reduced pressure. Water (20 mL) was added and the solid was separated by filtration, washed with water (30 mL) and dried under vacuum. Crude compound was purified by the Simpliflash system (5:20:75 methanol/ethyl acetate/CH2Cl2 as eluent) to give the title compound as an off-white solid. Yield: 0.22 g (38%). MP 237-238° C. 1H NMR (400 MHz, DMSO-d6): δ 11.83 (br s, 1H), 11.20 (s, 1H), 8.34 (s, 1H), 7.90 (d, J=8.2 Hz, 1H), 7.37 (d, J=8.6 Hz, 1H), 6.73 (d, J=1.9 Hz, 1H), 6.48 (d, J=1.9 Hz, 1H), 6.30 (s, 1H), 4.81 (t, J=5.1 Hz, 1H), 3.89 (s, 3H), 3.84 (s, 3H), 3.75 (q, J=6.63 Hz, 2H), 2.89 (t, J=7.0 Hz, 2H).

후처리

  1. temperaturecooled to room temperature
  2. customThe solvent was evaporated under reduced pressure
  3. additionWater (20 mL) was added
  4. customthe solid was separated by filtration
  5. washwashed with water (30 mL)
  6. customdried under vacuum
  7. customCrude compound was purified by the Simpliflash system (5:20:75 methanol/ethyl acetate/CH2Cl2 as eluent)

출처 및 근거

ORD 기록
ord-f2420849677545fb81bd9edcebdfdaa6
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238640B2

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