Acetic Anhydride → (E)-3-(4-Acetyl-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-methyl-N-(3-methylbenzofuran-2-ylmethyl)acrylamide

HRID 1879974ノート

反応式

HRID 1879974 の反応式
[CH3:1][N:2]([CH2:18][C:19]1[O:20][C:21]2[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=2[C:23]=1[CH3:24])[C:3](=[O:17])/[CH:4]=[CH:5]/[C:6]1[CH:16]=[N:15][C:9]2[NH:10][CH2:11][CH2:12][NH:13][CH2:14][C:8]=2[CH:7]=1.CCN(CC)CC.[C:36](OC(=O)C)(=[O:38])[CH3:37]>C(Cl)Cl>[C:36]([N:13]1[CH2:14][C:8]2[CH:7]=[C:6](/[CH:5]=[CH:4]/[C:3]([N:2]([CH3:1])[CH2:18][C:19]3[O:20][C:21]4[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=4[C:23]=3[CH3:24])=[O:17])[CH:16]=[N:15][C:9]=2[NH:10][CH2:11][CH2:12]1)(=[O:38])[CH3:37]

参加物

5

反応物 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 45487682(E)-N-Methyl-N-(3-methylbenzofuran-2-ylmethyl)-3-(2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylamide

生成物 1

HCID 24891457(E)-3-(4-Acetyl-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-methyl-N-(3-methylbenzofuran-2-ylmethyl)acrylamide収率 76%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of (E)-N-methyl-N-(3-methylbenzofuran-2-ylmethyl)-3-(2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylamide (105 mg, 0.280 mmol) in CH2Cl2 (6 mL) was treated with Et3N (0.05 mL, 0.36 mmol) followed by acetic anhydride (27 μL, 0.29 mmol). After stirring for 1.5 h, the mixture was diluted with CH2Cl2 (100 mL) and washed with H2O (25 mL). The organic layer was dried over Na2SO4, filtered and concentrated to a tan residue. Purification by flash column chromatography (silica gel, CH2Cl2/MeOH, 96:4) gave the title compound (89 mg, 76%) as a colorless residue and as a mixture of amide rotamers: MS (ESI) m/e 419 (M+H)+.

後処理

  1. washwashed with H2O (25 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated to a tan residue
  5. customPurification by flash column chromatography (silica gel, CH2Cl2/MeOH, 96:4)

出典と根拠

ORDレコード
ord-e41186d59014456c9522da6f79a00d85
出典データセット
uspto-grants-2012_11
特許番号
US08318720B2

反応ノート

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