Triphenylphosphine → 1-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-((4-(trifluoromethyl)-1,3-thiazol-2-yl)methoxy)pyridin-2(1H)-one

HRID 2203083Notes

Reaction equation

HRID 2203083 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]([OH:20])=[CH:16][C:15]4=[O:21])[CH:12]=[CH:13][C:6]=3[N:5]=2)[CH2:3][CH2:2]1.[F:22][C:23]([F:32])([F:31])[C:24]1[N:25]=[C:26]([CH2:29]O)[S:27][CH:28]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCCOC)=O)=NC(OCCOC)=O>C1COCC1.O>[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][CH2:29][C:26]5[S:27][CH:28]=[C:24]([C:23]([F:32])([F:31])[F:22])[N:25]=5)=[CH:16][C:15]4=[O:21])[CH:12]=[CH:13][C:6]=3[N:5]=2)[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 23560688(4-(Trifluoromethyl)-1,3-thiazol-2-yl)methanolHCID 533844152-methoxyethyl N-(2-methoxyethoxycarbonylimino)carbamateHCID 896910841-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-hydroxypyridin-2(1H)-one

Product 1

HCID 897025821-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-((4-(trifluoromethyl)-1,3-thiazol-2-yl)methoxy)pyridin-2(1H)-oneYield 33.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-hydroxypyridin-2(1H)-one (50 mg), (4-(trifluoromethyl)-1,3-thiazol-2-yl)methanol (65.1 mg) and triphenylphosphine (140 mg) in THF (5 ml) was added bis(2-methoxyethyl) azodicarboxylate (125 mg), and the mixture was stirred at room temperature for 3 h. The mixture was poured into water and extracted with EtOAc. The extract was washed with brine, dried over MgSO4, concentrated and purified by silica gel column chromatography (hexane/EtOAc then EtOAc/MeOH). The resulting solid was recrystallized from EtOH-hexane to give the title compound (26.5 mg) as a white solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe extract was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography (hexane/EtOAc
  6. customThe resulting solid was recrystallized from EtOH-hexane

Sources & evidence

ORD record
ord-5a2dda91628746fb9e8916981d130a83
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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