Difluoroacetic acid → N-(2,4-Dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-2,2-difluoro-acetamide

HRID 131355

Reaction equation

HRID 131355 reaction equation
[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][CH:16]([F:20])[C:17](O)=[O:18]>>[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:17](=[O:18])[CH:16]([F:20])[F:15]

Participants

3

Reactant 2

HCID 9788Difluoroacetic acidHCID 219558063-amino-1H-1,5-benzodiazepine-2,4(3H,5H)-dione

Product 1

HCID 58625869N-(2,4-Dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-2,2-difluoro-acetamide

Procedure

Using the method of Example 62, using 3-amino-1,5-dihydro-benzo[b][1,4]diazepine-2,4-dione and difluoroacetic acid, stirring overnight at ambient temperature after the addition of the acid, and washing reaction solid with dichloromethane instead of isopropanol: chloroform (3:1) gives the title compound: mass spectrum (APCI, m/e): 270 (M+1); NMR (1H, 300 MHz, DMSO-d6): δ 10.88 (s, 2H), 9.13 (d, 1H, J=6.9 Hz), 7.29-7.13 (m, 4H), 6.49 (t, 1H, 2J(H,F)=53.7 Hz), 4.79 (d, 1H, J=6.9 Hz).

Workup

  1. additionafter the addition of the acid
  2. washwashing
  3. customreaction solid with dichloromethane instead of isopropanol: chloroform (3:1)

Sources & evidence

ORD record
ord-00ebadea441e4acb8ea279c025013744
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Linked notes

Loading…