HCID 89690999, compound → HCID 89691194, compound

HRID 2203071Notes

Reaction equation

HRID 2203071 reaction equation
[CH:1]1([C:4]2[N:8]([CH3:9])[C:7]3[CH:10]=[C:11]([N:14]4[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]5[S:23][C:24]([F:28])=[C:25](F)[CH:26]=5)=[CH:16][C:15]4=[O:29])[CH:12]=[CH:13][C:6]=3[N:5]=2)[CH2:3][CH2:2]1.[Br:30]C1C=C(COC2C=CN(C3C=CC4N=C(C5CC5)N(C)C=4C=3)C(=O)C=2)SC=1>>[Br:30][C:25]1[CH:26]=[C:22]([CH2:21][O:20][C:17]2[CH:18]=[CH:19][N:14]([C:11]3[CH:12]=[CH:13][C:6]4[N:5]=[C:4]([CH:1]5[CH2:3][CH2:2]5)[N:8]([CH3:9])[C:7]=4[CH:10]=3)[C:15](=[O:29])[CH:16]=2)[S:23][C:24]=1[F:28]

Participants

3

Reactant 2

HCID 89690999HCID 89690999, compoundHCID 89691083HCID 89691083, compound

Product 1

HCID 89691194HCID 89691194, compound

Procedure

A mixture of the title compound, 1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-((4,5-difluoro-2-thienyl)methoxy)pyridin-2(1H)-one and 4-((4-bromo-2-thienyl)methoxy)-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one obtained in step D in example 219 was subjected to HPLC separation (C18, mobile phase: H2O/CH3CN (0.1% TFA included)). The solution was neutralized with saturated Na2CO3 solution and extracted with EtOAc. The organic layer was separated, washed with water and brine successively, dried over MgSO4, filtered through a plug of silica gel, and concentrated in vacuo. The residual solid was recrystallized from EtOH to give the title compound (10.0 mg) as an off-white solid.

Sources & evidence

ORD record
ord-0c66a49277aa41aeac4b519e928e9e22
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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