HCID 89690999, compound → HCID 89691083, compound

HRID 2203065Notes

Reaction equation

HRID 2203065 reaction equation
C1(C2N(C)C3C=C(N4C=CC(OCC5SC(F)=C(F)C=5)=CC4=O)C=CC=3N=2)CC1.[Br:30][C:31]1[CH:32]=[C:33]([CH2:37][O:38][C:39]2[CH:44]=[CH:43][N:42]([C:45]3[CH:46]=[CH:47][C:48]4[N:52]=[C:51]([CH:53]5[CH2:55][CH2:54]5)[N:50]([CH3:56])[C:49]=4[CH:57]=3)[C:41](=[O:58])[CH:40]=2)[S:34][C:35]=1F>>[Br:30][C:31]1[CH:32]=[C:33]([CH2:37][O:38][C:39]2[CH:44]=[CH:43][N:42]([C:45]3[CH:46]=[CH:47][C:48]4[N:52]=[C:51]([CH:53]5[CH2:54][CH2:55]5)[N:50]([CH3:56])[C:49]=4[CH:57]=3)[C:41](=[O:58])[CH:40]=2)[S:34][CH:35]=1

Participants

3

Reactant 2

HCID 89690999HCID 89690999, compoundHCID 89691194HCID 89691194, compound

Product 1

HCID 89691083HCID 89691083, 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-5-fluoro-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 (30.0 mg) as an off-white solid.

Sources & evidence

ORD record
ord-d27bda4e8e6e4142ba09df741510fa00
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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