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

HRID 591702ノート

反応式

HRID 591702 の反応式
[CH3:1][N:2]([CH2:4][C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([CH:14]=O)=[CH:9][CH:8]=2)[CH3:3].[NH2:16][C:17]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[C:22]([O:28][CH3:29])[C:18]=1[C:19]([NH2:21])=[O:20].S([O-])(O)=O.[Na+].C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C)C(=O)C>[CH3:3][N:2]([CH2:4][C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([C:14]1[NH:21][C:19](=[O:20])[C:18]3[C:17](=[CH:25][C:24]([O:26][CH3:27])=[CH:23][C:22]=3[O:28][CH3:29])[N:16]=1)=[CH:9][CH:8]=2)[CH3:1]

参加物

6

反応物 4

HCID 6101p-Toluenesulfonic acidHCID 203490162-Amino-4,6-dimethoxybenzamideHCID 23665763Sodium BisulfiteHCID 866620322-dimethylaminomethyl-1H-indole-5-carbaldehyde

生成物 1

HCID 1359390422-(2-((Dimethylamino)methyl)-1H-indol-5-yl)-5,7-dimethoxyquinazolin-4(3H)-one

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
120 °C

実験手順

To a solution of 2-dimethylaminomethyl-1H-indole-5-carbaldehyde (0.88 g crude, 4.35 mmol) and 2-amino-4,6-dimethoxy-benzamide (0.85 g, 4.35 mmol) in N,N-dimethylacetamide (15 mL) were added sodium hydrogen sulfite (58.5 wt %, 0.95 g, 5.22 mmol) and p-toluenesulfonic acid (0.99 g, 5.22 mmol). The reaction mixture was stirred at 120° C. for 5 hours under nitrogen, then cooled to room temperature, and concentrated under reduced pressure. 30% aqueous sodium carbonate (50 mL) was then added. The separated solid was filtered, washed with water (50 mL), and dried under vacuum. Crude compound was purified by the Simpliflash system (0-5% methanol in CH2Cl2 and 7 N ammonia in methanol 5% in CH2Cl2 as eluent) to give the title compound as an off-white solid. Yield: 0.83 g (50%). MP 187-188° C. 1H NMR (400 MHz, DMSO-d6): δ 11.82 (s, 1H), 11.34 (s, 1H), 8.38 (s, 1H), 7.93 (d, J=8.59 Hz, 1H), 7.40 (d, J=8.59 Hz, 1H), 6.73 (s, 1H), 6.49 (s, 1H), 6.40 (s, 1H), 3.90 (s, 3H), 3.85 (s, 3H), 3.57 (s, 2H), 2.21 (s, 6H).

後処理

  1. temperaturecooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. addition30% aqueous sodium carbonate (50 mL) was then added
  4. filtrationThe separated solid was filtered
  5. washwashed with water (50 mL)
  6. customdried under vacuum
  7. customCrude compound was purified by the Simpliflash system (0-5% methanol in CH2Cl2 and 7 N ammonia in methanol 5% in CH2Cl2 as eluent)

出典と根拠

ORDレコード
ord-e70bb02dfda941609b4523109f91e97b
出典データセット
uspto-grants-2016_01
特許番号
US09238640B2

反応ノート

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