N-(((3R,4S)-4-Fluoropyrrolidin-3-yl)methyl)cyclopropanamine → HCID 86609603, compound

HRID 424745Notes

Reaction equation

HRID 424745 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1F)[N:8]([CH2:13][CH2:14][F:15])[CH:7]=[C:6]([C:16]([OH:18])=[O:17])[C:5]2=[O:19].[CH:20]1([NH:23][CH2:24][C@@H:25]2[C@H:29]([F:30])[CH2:28][NH:27][CH2:26]2)[CH2:22][CH2:21]1>>[CH:20]1([NH:23][CH2:24][C@@H:25]2[C@H:29]([F:30])[CH2:28][N:27]([C:11]3[CH:10]=[C:9]4[C:4]([C:5](=[O:19])[C:6]([C:16]([OH:18])=[O:17])=[CH:7][N:8]4[CH2:13][CH2:14][F:15])=[CH:3][C:2]=3[F:1])[CH2:26]2)[CH2:22][CH2:21]1

Participants

3

Reactant 2

HCID 11147857N-(((3R,4S)-4-Fluoropyrrolidin-3-yl)methyl)cyclopropanamineHCID 144238546,7-Difluoro-1-(2-fluoroethyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 86609603HCID 86609603, compoundYield 45.5%

Procedure

Using 6,7-difluoro-1-(2-fluoroethyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (271 mg) and (3R,4S)-3-cyclopropylaminomethyl-4-fluoropyrrolidine (174 mg), the same procedure was followed as in Example 23 to give 7-[(3S,4S)-3-cyclopropylaminomethyl-4-fluoro-1-pyrrolidinyl]-6-fluoro-1-(2-fluoroethyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid as a pale yellow powder (186 mg).

Sources & evidence

ORD record
ord-21254b1d3eed4379860709becc216e41
Source dataset
uspto-grants-2012_01
Patent number
US08106072B2

Reaction notes

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