4,4,4-Trifluorobutanoic acid → N-(2,4-Dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazapin-3-yl)-4,4,4-trifluoro-butyramide

HRID 131356

반응식

HRID 131356 반응식
[NH2:1][CH:2]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[NH:4][C:3]1=[O:14].[F:15][C:16]([F:23])([F:22])[CH2:17][CH2:18][C:19](O)=[O:20]>CN(C)C1C=CN=CC=1.CN(C=O)C>[O:9]=[C:8]1[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[NH:4][C:3](=[O:14])[CH:2]1[NH:1][C:19](=[O:20])[CH2:18][CH2:17][C:16]([F:23])([F:22])[F:15]

참가 물질

5

반응물 2

HCID 27770854,4,4-Trifluorobutanoic acidHCID 219558063-amino-1H-1,5-benzodiazepine-2,4(3H,5H)-dione

생성물 1

HCID 58626040N-(2,4-Dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazapin-3-yl)-4,4,4-trifluoro-butyramide수율 74%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매

실험 절차

Combine 3-amino-1H-1,5-benzodiazepine-2,4-(3H, 5H)-dione (5.60 g, 29.3 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimde hydrochloride (6.75 g, 35.2 mmol) and 4(dimethylamino)pyridine (0.183 g, 1.5 mmol) in 100 mL DMF, add 4,4,4-trifluoro butyric acid dropwise at 0-5° C. After addition, stir the reaction mixture at ice-water. After half an hour, warm to RT. After stirring overnight, remove solvent DMF under reduce pressure and suspend the residue in 200 mL of mixed solvent (CHCl3: i-PrOH=3:1). Collect the solid via vacuum filtration to give the title compound (6.87 g, yield 74%): mass spectrum (APCI) (m/e): 316.1 (M+1); 1H NMR (400 MHz, DMSO-d6): δ 10.72 (s, 2H), 8.60 (d, 1H, J=7.2 Hz), 7.24-7.15 (m, 4H), 4.74 (d, 1H, J=7.2 Hz), 2.58 (t, 2H, J=7.2 Hz), 2.39-2.35 (m, 2H).

후처리

  1. additionAfter addition
  2. waitAfter half an hour
  3. customremove solvent DMF
  4. customCollect the solid
  5. filtrationvia vacuum filtration

출처 및 근거

ORD 기록
ord-de96973e6ca942bba5431d5ecdb42ab3
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384934B2

연결된 노트

불러오는 중…