HCID 118045775, compound → HCID 118045771, compound

HRID 595891Notes

Reaction equation

HRID 595891 reaction equation
[NH2:1][C:2]1[C:3]([C:12]2[CH:27]=[CH:26][C:15]([C:16]([NH:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])=[C:14]([F:28])[CH:13]=2)=[N:4][C:5]([CH2:8][CH:9]([OH:11])[CH3:10])=[CH:6][N:7]=1>CO>[NH2:1][C:2]1[C:3]([C:12]2[CH:27]=[CH:26][C:15]([C:16]([NH:18][CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[O:17])=[C:14]([F:28])[CH:13]=2)=[N:4][C:5]([CH2:8][C@H:9]([OH:11])[CH3:10])=[CH:6][N:7]=1

Participants

3

Reactant 1

HCID 118045775HCID 118045775, compound

Product 1

HCID 118045771HCID 118045771, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The racemic (+/−)-4-(3-amino-6-(2-hydroxypropyl)pyrazin-2-yl)-N-benzyl-2-fluorobenzamide was resolved by chiral SFC (ChiralPak 5mic AD column, 4.6×100 (mm), methanol+0.1% DEA=40%, 5 mL/min). The polar enantiomer, (R)-4-(3-amino-6-(2-hydroxypropyl)pyrazin-2-yl)-N-benzyl-2-fluorobenzamide, was obtained at Rt=1.39 min. LCMS (m/z): 381.2 (MH+), 0.67 min. The less polar enantiomer, (S)-4-(3-amino-6-(2-hydroxypropyl)pyrazin-2-yl)-N-benzyl-2-fluorobenzamide was obtained at Rt=1.97 min. LCMS (m/z): 381.2 (MH+), 0.67 min. The stereochemistry was assigned arbitrarily.

Sources & evidence

ORD record
ord-487b4da717164c69b707a095b7139d70
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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