2-methoxy-N-(2,2,3,3,3-pentafluoro-propyl)-malonamic acid → (-)-2-methoxy-N-(6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-N'-(2,2,3,3,3-pentafluoro-propyl)-malonamide

HRID 1372944Notes

Reaction equation

HRID 1372944 reaction equation
[NH2:1][C@@H:2]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[C:4]2[CH:14]=[CH:15][CH:16]=[CH:17][C:3]1=2.[CH3:18][O:19][CH:20]([C:24]([NH:26][CH2:27][C:28]([F:34])([F:33])[C:29]([F:32])([F:31])[F:30])=[O:25])[C:21](O)=[O:22]>>[CH3:18][O:19][CH:20]([C:24]([NH:26][CH2:27][C:28]([F:33])([F:34])[C:29]([F:30])([F:31])[F:32])=[O:25])[C:21]([NH:1][CH:2]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[C:4]2[CH:14]=[CH:15][CH:16]=[CH:17][C:3]1=2)=[O:22]

Participants

3

Reactant 2

HCID 210724932-methoxy-N-(2,2,3,3,3-pentafluoro-propyl)-malonamic acidHCID 25067537(7S)-7-Amino-5,7-dihydro-6H-dibenzo[b,d]azepin-6-one

Product 1

HCID 11155654(-)-2-methoxy-N-(6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-N'-(2,2,3,3,3-pentafluoro-propyl)-malonamide

Procedure

(S)-7-Amino-5H,7H-dibenzo[b,d]azepin-6-one was coupled with 2-methoxy-N-(2,2,3,3,3-pentafluoro-propyl)-malonamic acid in analogy to the description in examples 65 and 66 to yield (−)-2-methoxy-N-(6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-N′-(2,2,3,3,3-pentafluoro-propyl)-malonamide as white solid,

Sources & evidence

ORD record
ord-3def7af7f2244e04a7686278855475e7
Source dataset
uspto-grants-2007_01
Patent number
US07160875B2

Reaction notes

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