N-(Tetrahydro-2H-pyran-4-yl)-N-[3-(trifluoromethoxy)benzyl]imidazo[1,2-a]pyridine-2-carboxamide → N-(Tetrahydro-2H-pyran-4-yl)-N-[3-(trifluoromethoxy)benzyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carboxamide

HRID 467963Notes

Reaction equation

HRID 467963 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([N:7]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][C:27]([F:30])([F:29])[F:28])[CH:21]=2)[C:8]([C:10]2[N:11]=[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]3[CH:18]=2)=[O:9])[CH2:3][CH2:2]1>[C].[Pd].CO>[O:1]1[CH2:6][CH2:5][CH:4]([N:7]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][C:27]([F:28])([F:29])[F:30])[CH:21]=2)[C:8]([C:10]2[N:11]=[C:12]3[CH2:17][CH2:16][CH2:15][CH2:14][N:13]3[CH:18]=2)=[O:9])[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 58049370N-(Tetrahydro-2H-pyran-4-yl)-N-[3-(trifluoromethoxy)benzyl]imidazo[1,2-a]pyridine-2-carboxamide

Product 1

HCID 46916730N-(Tetrahydro-2H-pyran-4-yl)-N-[3-(trifluoromethoxy)benzyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carboxamideYield 95.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-(tetrahydro-2H-pyran-4-yl)-N-[3-(trifluoromethoxy)benzyl]imidazo[1,2-a]pyridine-2-carboxamide (50 mg), 10% palladium-carbon (50 mg) and methanol (15 mL) was stirred in a nitrogen atmosphere for 2 hours at room temperature. The insoluble matter was filtered off and methanol was distilled off under reduced pressure to give the titled compound (48 mg).

Workup

  1. filtrationThe insoluble matter was filtered off
  2. distillationmethanol was distilled off under reduced pressure

Sources & evidence

ORD record
ord-d15a8106b1404230a679aa89ae608dfc
Source dataset
uspto-grants-2014_01
Patent number
US08623898B2

Reaction notes

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