N-(((3R,4S)-4-Fluoropyrrolidin-3-yl)methyl)cyclopropanamine → HCID 66705037, compound

HRID 424761Notes

Reaction equation

HRID 424761 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:13])[C:11]=1F)[N:8]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:7]=[C:6]([C:18]([O:20]CC)=[O:19])[C:5]2=[O:23].[CH:24]1([NH:27][CH2:28][C@@H:29]2[C@H:33]([F:34])[CH2:32][NH:31][CH2:30]2)[CH2:26][CH2:25]1>>[CH:24]1([NH:27][CH2:28][C@@H:29]2[C@H:33]([F:34])[CH2:32][N:31]([C:11]3[C:10]([F:13])=[C:9]4[C:4]([C:5](=[O:23])[C:6]([C:18]([OH:20])=[O:19])=[CH:7][N:8]4[C:14]([CH3:15])([CH3:16])[CH3:17])=[CH:3][C:2]=3[F:1])[CH2:30]2)[CH2:26][CH2:25]1

Participants

3

Reactant 2

HCID 11147857N-(((3R,4S)-4-Fluoropyrrolidin-3-yl)methyl)cyclopropanamineHCID 14839591HCID 14839591, compound

Product 1

HCID 66705037HCID 66705037, compoundYield 37.6%

Procedure

Using ethyl 6,7,8-trifluoro-1,4-dihydro-1-(1,1-dimethylethyl)-4-oxo-3-quinolinecarboxylate (50.0 mg) and (3R,4S)-3-cyclopropylaminomethyl-4-fluoropyrrolidine (29.0 mg), the same procedure was followed as in Example 40 to give 7-[(3S,4S)-3-cyclopropylaminomethyl-4-fluoro-1-pyrrolidinyl]-6,8-difluoro-1,4-dihydro-1-(1,1-dimethylethyl)-4-oxo-3-quinolinecarboxylic acid as a pale yellow powder (25.1 mg).

Sources & evidence

ORD record
ord-df8f052bdd494fb8857b2fd84cd431aa
Source dataset
uspto-grants-2012_01
Patent number
US08106072B2

Reaction notes

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