Acetic Anhydride → HCID 57974361、化合物

HRID 1864344ノート

反応式

HRID 1864344 の反応式
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH3:8][NH:9][C@H:10]([CH3:39])[CH2:11][O:12][C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[C:15]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][C:31]3[CH:32]=[N:33][C:34]([CH3:37])=[CH:35][CH:36]=3)=[C:26]([CH3:38])[CH:25]=1)=[N:16][CH:17]=[N:18]2.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:8][N:9]([C@H:10]([CH3:39])[CH2:11][O:12][C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[C:15]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][C:31]3[CH:32]=[N:33][C:34]([CH3:37])=[CH:35][CH:36]=3)=[C:26]([CH3:38])[CH:25]=1)=[N:16][CH:17]=[N:18]2)[C:1](=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 69064879HCID 69064879、化合物

生成物 1

HCID 57974361HCID 57974361、化合物収率 84.1%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

Acetic anhydride (66 μl, 0.70 mmol) was added drop wise to a solution of 5-{[(2R)-2-(methylamino)propyl]oxy}-N-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}quinazolin-4-amine (250 mg, 0.58 mmol, obtained as described in Example 115, preparation of starting materials) and potassium carbonate (161 mg, 1.16 mmol) in acetone (10 ml). The mixture was stirred at room temperature for 2 hours. After evaporation of the solvents, the residue was diluted in DCM. The solution washed with aqueous sodium bicarbonate and dried over magnesium sulfate. After evaporation of the solvents, the residue was purified by chromatography on silica gel (eluant: 2 to 5% 7N ammonia-methanol in DCM) to give the title compound (230 mg, 84%); NMR Spectrum: (CDCl3) 1.28 (d, 3H), 1.94 (s, 3H), 2.30 (s, 3H), 2.53 (s, 3H), 2.90 (s, 3H), 4.30-4.10 (m, 2H), 5.38 (m, 1H), 6.92 (m, 2H), 7.08 (d, 1H), 7.14 (dd, 1H), 7.48 (d, 2H), 7.53 (s, 1H), 7.64 (t, 1H), 8.27 (d, 1H), 8.60 (s, 1H), 9.51 (s, 1H); Mass spectrum: MH+ 472.

後処理

  1. customAfter evaporation of the solvents
  2. additionthe residue was diluted in DCM
  3. washThe solution washed with aqueous sodium bicarbonate
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation of the solvents
  6. customthe residue was purified by chromatography on silica gel (eluant: 2 to 5% 7N ammonia-methanol in DCM)

出典と根拠

ORDレコード
ord-671891d25694480289815b602b3a3a37
出典データセット
uspto-grants-2009_12
特許番号
US07625908B2

反応ノート

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