(Rac)-2,5-dibromo-n,n-dimethyl-pentanamide → (Rac)-5-bromo-2-[7-oxo-4-(3-trifluoromethyl-phenyl)-[1,4]diazepan-1-yl]-pentanoic acid dimethylamide

HRID 1096225Notes

Reaction equation

HRID 1096225 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([N:9]2[CH2:15][CH2:14][C:13](=[O:16])[NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.Br[CH:20]([CH2:26][CH2:27][CH2:28][Br:29])[C:21]([N:23]([CH3:25])[CH3:24])=[O:22]>>[CH3:24][N:23]([CH3:25])[C:21](=[O:22])[CH:20]([N:12]1[C:13](=[O:16])[CH2:14][CH2:15][N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:17])[F:18])[CH:4]=2)[CH2:10][CH2:11]1)[CH2:26][CH2:27][CH2:28][Br:29]

Participants

3

Reactant 2

HCID 20370625(Rac)-2,5-dibromo-n,n-dimethyl-pentanamide2×HCID 217545091-(3-Trifluoromethyl-phenyl)-[1,4]diazepan-5-one

Product 1

HCID 66783239(Rac)-5-bromo-2-[7-oxo-4-(3-trifluoromethyl-phenyl)-[1,4]diazepan-1-yl]-pentanoic acid dimethylamideYield 73%

Procedure

In analogy to the procedure described in example 15B, 1-(3-trifluoromethyl-phenyl)-[1,4]diazepan-5-one (example 15 A) and (rac)-2,5-dibromo-N,N-dimethyl-pentanamide (intermediate 9) gave the title compound in 73% yield as light yellow oil. MS: 466.2 (1Br, MH+).

Sources & evidence

ORD record
ord-09c0c87da54a44cbb39bd98caa433680
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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