Pyridine → HCID 89691230, compound

HRID 2202924Notes

Reaction equation

HRID 2202924 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[Cl:14][C:15]1[CH:45]=[CH:44][C:18]([CH2:19][O:20][C:21]2[CH:26]=[CH:25][N:24]([C:27]3[CH:28]=[CH:29][C:30]4[N:34]=[C:33]([CH:35]5[CH2:37][CH:36]5[C:38]([NH2:40])=O)[N:32]([CH3:41])[C:31]=4[CH:42]=3)[C:23](=[O:43])[CH:22]=2)=[CH:17][CH:16]=1.N1C=CC=CC=1>C1COCC1>[Cl:14][C:15]1[CH:45]=[CH:44][C:18]([CH2:19][O:20][C:21]2[CH:26]=[CH:25][N:24]([C:27]3[CH:28]=[CH:29][C:30]4[N:34]=[C:33]([CH:35]5[CH2:37][CH:36]5[C:38]#[N:40])[N:32]([CH3:41])[C:31]=4[CH:42]=3)[C:23](=[O:43])[CH:22]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 89690958HCID 89690958, compound

Product 1

HCID 89691230HCID 89691230, compoundYield 13.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Trifluoroacetic anhydride (0.109 ml) was added to a solution of (1RS,2RS)-2-(6-(4-((4-chlorobenzyl)oxy)-2-oxopyridin-1(2H)-yl)-1-methyl-1H-benzimidazol-2-yl)cyclopropanecarboxamide (117 mg) and pyridine (0.063 ml) in THF (3 ml) at 0° C. The mixture was stirred at 0° C. under Ar atmosphere for 1 h. The mixture was quenched with saturated NaHCO3 solution at 0° C. and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The resulting solid was crystallized from THF/hexane to give the title compound (15 mg) as an off-white solid.

Workup

  1. customThe mixture was quenched with saturated NaHCO3 solution at 0° C.
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe resulting solid was crystallized from THF/hexane

Sources & evidence

ORD record
ord-0faced8e43b8486b9aeb1014f7fd7c99
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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