2-methyl-N-(3,3,4,4,4-pentafluoro-butyl)-malonamic acid → N-((S)-5-cyclopropylmethyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-2-methyl-N'-(3,3,4,4,4-pentafluoro-butyl)-malonamide

HRID 1372955Notes

Reaction equation

HRID 1372955 reaction equation
[NH2:1][C@@H:2]1[C:8](=[O:9])[N:7]([CH2:10][CH:11]2[CH2:13][CH2:12]2)[C:6]2[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=2[C:4]2[CH:18]=[CH:19][CH:20]=[CH:21][C:3]1=2.[CH3:22][CH:23]([C:27]([NH:29][CH2:30][CH2:31][C:32]([F:38])([F:37])[C:33]([F:36])([F:35])[F:34])=[O:28])[C:24](O)=[O:25]>>[CH:11]1([CH2:10][N:7]2[C:8](=[O:9])[C@@H:2]([NH:1][C:24](=[O:25])[CH:23]([CH3:22])[C:27]([NH:29][CH2:30][CH2:31][C:32]([F:37])([F:38])[C:33]([F:36])([F:34])[F:35])=[O:28])[C:3]3[CH:21]=[CH:20][CH:19]=[CH:18][C:4]=3[C:5]3[CH:17]=[CH:16][CH:15]=[CH:14][C:6]2=3)[CH2:13][CH2:12]1

Participants

3

Reactant 2

HCID 210724972-methyl-N-(3,3,4,4,4-pentafluoro-butyl)-malonamic acidHCID 68916092HCID 68916092, compound

Product 1

HCID 86596826N-((S)-5-cyclopropylmethyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-2-methyl-N'-(3,3,4,4,4-pentafluoro-butyl)-malonamide

Procedure

(S)-7-amino-5-cyclopropylmethyl-5H,7H-dibenzo[b,d]azepin-6-one was coupled with 2-methyl-N-(3,3,4,4,4-pentafluoro-butyl)-malonamic acid in analogy to the description in example 73 to yield N-((S)-5-cyclopropylmethyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-2-methyl-N′-(3,3,4,4,4-pentafluoro-butyl)-malonamide (epimers) as white solid.

Sources & evidence

ORD record
ord-884491159d104a21a61150272e3b156e
Source dataset
uspto-grants-2007_01
Patent number
US07160875B2

Reaction notes

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