HCID 118061136, compound → HCID 118060876, compound

HRID 632820Notes

Reaction equation

HRID 632820 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]([C:10]2[N:11]=[C:12]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH:21][CH2:22][C:23]([F:26])([F:25])[F:24])[CH:16]=3)[O:13][CH:14]=2)=[O:9])[C:4]([N:27]2[CH2:31][CH2:30][CH:29]([CH3:32])[C:28]2=[O:33])=[N:3]1>CCCCCC.C(O)C>[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]([C:10]2[N:11]=[C:12]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH:21][CH2:22][C:23]([F:25])([F:26])[F:24])[CH:16]=3)[O:13][CH:14]=2)=[O:9])[C:4]([N:27]2[CH2:31][CH2:30][C@H:29]([CH3:32])[C:28]2=[O:33])=[N:3]1

Participants

3

Reactant 1

HCID 118061136HCID 118061136, compound

Product 1

HCID 118060876HCID 118060876, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 21879635Ethanol hexaneSolvent

Procedure

Racemic N-(1-methyl-3-(3-methyl-2-oxopyrrolidin-1-yl)-1H-pyrazol-4-yl)-2-(2-((2,2,2-trifluoroethyl)amino)pyridin-4-yl)-1,3-oxazole-4-carboxamide (399 mg) was resolved by HPLC (column: CHIRALPAK IA (trade name), 50 mmID×500 mL, manufactured by Daicel Chemical Industries, mobile phase: hexane/ethanol=500/500), and the compound (186.7 mg) having a shorter retention time was recrystallized from THF/diisopropyl ether to give the title compound (183.7 mg).

Workup

  1. customwas recrystallized from THF/diisopropyl ether

Sources & evidence

ORD record
ord-edcf0c7bdc484436a58cf9ba3c69aa7b
Source dataset
uspto-grants-2016_04
Patent number
US09321757B2

Reaction notes

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