Acetic Anhydride → [2-(N-Methyl-acetamido)-quinazolin-4-yl]-(4-dimethylaminophenyl)-methylamine

HRID 2381011ノート

反応式

HRID 2381011 の反応式
[CH3:1][NH:2][C:3]1[N:12]=[C:11]([N:13]([C:15]2[CH:20]=[CH:19][C:18]([N:21]([CH3:23])[CH3:22])=[CH:17][CH:16]=2)[CH3:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[C:40](OC(=O)C)(=[O:42])[CH3:41]>C(Cl)Cl.C(OCC)(=O)C>[CH3:1][N:2]([C:3]1[N:12]=[C:11]([N:13]([C:15]2[CH:16]=[CH:17][C:18]([N:21]([CH3:22])[CH3:23])=[CH:19][CH:20]=2)[CH3:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)[C:40](=[O:42])[CH3:41]

参加物

7

反応物 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 11638105(2-Methylamino-quinazolin-4-yl)-(4-dimethylaminophenyl)-methylamine

生成物 1

HCID 11710027[2-(N-Methyl-acetamido)-quinazolin-4-yl]-(4-dimethylaminophenyl)-methylamine収率 85%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To a solution of (2-methylamino-quinazolin-4-yl)-(4-dimethylaminophenyl)-methylamine (40 mg, 0.13 mmol) in 4 mL of methylenechloride cooled at 0° C. was added triethylamine (50 uL, 0.36 mmol), few crystals of dimethylaminopyridine and acetic anhydride (50 uL, 0.53 mmol). The reaction mixture was stirred for 1 h at 0° C., warmed to room temperature, and stirred overnight. The reaction mixture was diluted with 25 mL of ethyl acetate and washed with 25 mL of saturated sodium bicarbonate. The organic layer was dried over anhydrous NaSO4, filtered and concentrated. The residue was purified by chromatography (40% ethyl acetate/hexane) to give the title compound (39 mg, 0.11 mmol, 85%). 1H NMR (CDCl3): 7.65-7.69 (m, 1H), 7.52 (ddd, J=8.4, 6.6, 1.8, 1H), 6.93-7.12 (m, 4H), 6.72 (m, 2H), 3.56 (s, 3H), 3.01 (s, 6H), 2.52 (s, 3H).

後処理

  1. temperaturewarmed to room temperature
  2. stirringstirred overnight
  3. washwashed with 25 mL of saturated sodium bicarbonate
  4. dry with materialThe organic layer was dried over anhydrous NaSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (40% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-61393c24458e4eb89aab7f3cd39e15e1
出典データセット
uspto-grants-2012_09
特許番号
US08258145B2

反応ノート

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