Hydrochloric Acid → HCID 86596818, compound

HRID 1372936Notes

Reaction equation

HRID 1372936 reaction equation
[CH3:1][CH:2]([C:19]([NH:21][CH2:22][C:23]([F:29])([F:28])[C:24]([F:27])([F:26])[F:25])=[O:20])[C:3]([NH:5][C@@H:6]1[C:12](=[O:13])[N:11]([CH3:14])[C:10]2[CH:15]=[CH:16][CH:17]=[CH:18][C:9]=2[NH:8][CH2:7]1)=[O:4].ClCCl.[C:33](Cl)(=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.Cl>C(N(CC)CC)C>[C:33]([N:8]1[CH2:7][C@H:6]([NH:5][C:3](=[O:4])[CH:2]([CH3:1])[C:19]([NH:21][CH2:22][C:23]([F:29])([F:28])[C:24]([F:26])([F:25])[F:27])=[O:20])[C:12](=[O:13])[N:11]([CH3:14])[C:10]2[CH:15]=[CH:16][CH:17]=[CH:18][C:9]1=2)(=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 7412Benzoyl chlorideHCID 86596819HCID 86596819, compound

Product 1

HCID 86596818HCID 86596818, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of 0.2 g (0.47 mmol) of 2-methyl-N-((3S)-1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-N′-(2,2,3,3,3-pentafluoro-propyl)-malonamide in 3 ml of dichloromethane 0.096 g (0.95 mmol) of triethylamine and 0.08 mg (0.57 mmol) of benzoylchloride were added. The mixture was stirred for 20 min at room temperature. Hydrochloric acid (10 ml of a 1 N solution) was added and the mixture was extracted two times with dichloromethane. The combined organic layers were extracted with 1N sodiumbicarbonate solution, dried (MgSO4) and concentrated in vacuo. The remaining oil was purified by column chromatography to yield 0.15 g (60%) of a white foam.

Workup

  1. extractionthe mixture was extracted two times with dichloromethane
  2. extractionThe combined organic layers were extracted with 1N sodiumbicarbonate solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe remaining oil was purified by column chromatography

Sources & evidence

ORD record
ord-f2d7059aab2d47198b05e9946ad6f002
Source dataset
uspto-grants-2007_01
Patent number
US07160875B2

Reaction notes

Loading…