2,2,3,3,3-Pentafluoropropylamine → (R)-N-((S)-5-cyclopropylmethyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-2-fluoro-2-methyl-N'-(2,2,3,3,3-pentafluoro-propyl)-malonamide

HRID 1372951Notes

Reaction equation

HRID 1372951 reaction equation
[CH:1]1([CH2:4][N:5]2[C:11](=[O:12])[C@@H:10]([NH:13][C:14](=[O:21])[C@@:15]([F:20])([CH3:19])[C:16]([OH:18])=O)[C:9]3[CH:22]=[CH:23][CH:24]=[CH:25][C:8]=3[C:7]3[CH:26]=[CH:27][CH:28]=[CH:29][C:6]2=3)[CH2:3][CH2:2]1.[F:30][C:31]([F:38])([C:34]([F:37])([F:36])[F:35])[CH2:32][NH2:33]>>[CH:1]1([CH2:4][N:5]2[C:11](=[O:12])[C@@H:10]([NH:13][C:14](=[O:21])[C@@:15]([F:20])([CH3:19])[C:16]([NH:33][CH2:32][C:31]([F:38])([F:30])[C:34]([F:37])([F:36])[F:35])=[O:18])[C:9]3[CH:22]=[CH:23][CH:24]=[CH:25][C:8]=3[C:7]3[CH:26]=[CH:27][CH:28]=[CH:29][C:6]2=3)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 790022,2,3,3,3-PentafluoropropylamineHCID 69043616HCID 69043616, compound

Product 1

HCID 21072479(R)-N-((S)-5-cyclopropylmethyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-2-fluoro-2-methyl-N'-(2,2,3,3,3-pentafluoro-propyl)-malonamide

Procedure

(S)-N-((S)-5-cyclopropylmethyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-2-fluoro-2-methyl-malonamic acid was coupled with 2,2,3,3,3-pentafluoropropylamine in analogy to the procedure described for RJR 7 to yield (R)-N-((S)-5-cyclopropylmethyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-2-fluoro-2-methyl-N′-(2,2,3,3,3-pentafluoro-propyl)-malonamide as white solid.

Sources & evidence

ORD record
ord-7794a0ac33d6445698bef0f87c39497f
Source dataset
uspto-grants-2007_01
Patent number
US07160875B2

Reaction notes

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