HCID 118045361, compound → HCID 118045348, compound

HRID 595946Notes

Reaction equation

HRID 595946 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[CH:25]=[CH:24][C:11]([C:12]([NH:14][C@H:15]3[CH2:17][C@@H:16]3[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:13])=[C:10]([F:26])[CH:9]=2)=[CH:6][C:5]([Br:27])=[CH:4][N:3]=1>CCO>[NH2:1][C:2]1[C:7]([C:8]2[CH:25]=[CH:24][C:11]([C:12]([NH:14][C@@H:15]3[CH2:17][C@H:16]3[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:13])=[C:10]([F:26])[CH:9]=2)=[CH:6][C:5]([Br:27])=[CH:4][N:3]=1

Participants

3

Reactant 1

HCID 118045361HCID 118045361, compound

Product 1

HCID 118045348HCID 118045348, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(+/−)-4-(2-amino-5-bromopyridin-3-yl)-2-fluoro-N-((1S,2R)-2-phenylcyclopropyl)benzamide (121 mg) was resolved by chrial chromatography (AD-H column EtOH=60/40, 1 mL/min). The polar compound (Peak1), 4-(2-amino-5-bromopyridin-3-yl)-2-fluoro-N-((1R,2S)-2-phenylcyclopropyl)benzamide, was obtained at 7.41 min (50 mg, 41%) and the less polar compound (Peak2), 4-(2-amino-5-bromopyridin-3-yl)-2-fluoro-N-((1S,2R)-2-phenylcyclopropyl)benzamide, was obtained at 10.26 min (54 mg, 44%). The absolute stereochemistry was assigned based on biochemical data and docking model of the corresponding analogs.

Sources & evidence

ORD record
ord-9f279575a6f9432d85695e6af0283182
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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