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 340827노트

반응식

HRID 340827 반응식
[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]

참가 물질

5

반응물 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

생성물 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)acrylamide수율 76%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-03671de67e0a46e9a9fa63050854063b
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895545B2

반응 노트

불러오는 중…