N-(((3R,4S)-4-Fluoropyrrolidin-3-yl)methyl)cyclopropanamine → HCID 66704665, compound

HRID 424760Notes

Reaction equation

HRID 424760 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1F)[N:8]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:7]=[C:6]([C:17]([O:19]CC)=[O:18])[C:5]2=[O:22].[CH:23]1([NH:26][CH2:27][C@@H:28]2[C@H:32]([F:33])[CH2:31][NH:30][CH2:29]2)[CH2:25][CH2:24]1>>[CH:23]1([NH:26][CH2:27][C@@H:28]2[C@H:32]([F:33])[CH2:31][N:30]([C:11]3[CH:10]=[C:9]4[C:4]([C:5](=[O:22])[C:6]([C:17]([OH:19])=[O:18])=[CH:7][N:8]4[C:13]([CH3:14])([CH3:16])[CH3:15])=[CH:3][C:2]=3[F:1])[CH2:29]2)[CH2:25][CH2:24]1

Participants

3

Reactant 2

HCID 11147857N-(((3R,4S)-4-Fluoropyrrolidin-3-yl)methyl)cyclopropanamineHCID 14612522HCID 14612522, compound

Product 1

HCID 66704665HCID 66704665, compoundYield 21.8%

Procedure

Using ethyl 6,7-difluoro-1,4-dihydro-1-(1,1-dimethylethyl)-4-oxo-3-quinolinecarboxylate (309 mg) and (3R,4S)-3-cyclopropylaminomethyl-4-fluoropyrrolidine (174 mg), the same procedure was followed as in Example 40 to give 7-[(3S,4S)-3-cyclopropylaminomethyl-4-fluoro-1-pyrrolidinyl]-6-fluoro-1,4-dihydro-1-(1,1-dimethylethyl)-4-oxo-3-quinolinecarboxylic acid as pale yellow crystals (91.3 mg).

Sources & evidence

ORD record
ord-51ef01fd01774c79a1db812fc5f03120
Source dataset
uspto-grants-2012_01
Patent number
US08106072B2

Reaction notes

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