N-(((3R,4S)-4-Fluoropyrrolidin-3-yl)methyl)cyclopropanamine → HCID 66704781, compound

HRID 424753Notes

Reaction equation

HRID 424753 reaction equation
Cl[C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:19])[C:7]([C:16]([OH:18])=[O:17])=[CH:8][N:9]2[C@@H:12]2[CH2:14][C@@H:13]2[F:15])=[CH:4][C:3]=1[F:20].[CH:21]1([NH:24][CH2:25][C@@H:26]2[C@H:30]([F:31])[CH2:29][NH:28][CH2:27]2)[CH2:23][CH2:22]1>>[CH:21]1([NH:24][CH2:25][C@@H:26]2[C@H:30]([F:31])[CH2:29][N:28]([C:2]3[N:11]=[C:10]4[C:5]([C:6](=[O:19])[C:7]([C:16]([OH:18])=[O:17])=[CH:8][N:9]4[C@@H:12]4[CH2:14][C@@H:13]4[F:15])=[CH:4][C:3]=3[F:20])[CH2:27]2)[CH2:23][CH2:22]1

Participants

3

Reactant 2

HCID 11147857N-(((3R,4S)-4-Fluoropyrrolidin-3-yl)methyl)cyclopropanamineHCID 53884061HCID 53884061, compound

Product 1

HCID 66704781HCID 66704781, compoundYield 35.9%

Procedure

Using 7-chloro-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid (200 mg) and (3R,4S)-3-cyclopropylaminomethyl-4-fluoropyrrolidine (116 mg), the same procedure was followed as in Example 23 to give 7-[(3S,4S)-3-cyclopropylaminomethyl-4-fluoro-1-pyrrolidinyl]-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid as pale yellow crystals (101 mg).

Sources & evidence

ORD record
ord-83181471f3db44bab345d6d3d51c7685
Source dataset
uspto-grants-2012_01
Patent number
US08106072B2

Reaction notes

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