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

HRID 467954Notes

Reaction equation

HRID 467954 reaction equation
[F:1][C:2]([F:19])([F:18])[O:3][C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[CH2:7][NH:8][CH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.[N:20]1[C:21]([C:29](O)=[O:30])=[CH:22][N:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=12.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>C(N(CC)CC)C.CN(C)C=O>[O:12]1[CH2:13][CH2:14][CH:9]([N:8]([CH2:7][C:6]2[CH:15]=[CH:16][CH:17]=[C:4]([O:3][C:2]([F:18])([F:1])[F:19])[CH:5]=2)[C:29]([C:21]2[N:20]=[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][N:23]3[CH:22]=2)=[O:30])[CH2:10][CH2:11]1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 2062168Imidazo[1,2-a]pyridine-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58049381N-[3-(Trifluoromethoxy)benzyl]tetrahydro-2H-pyran-4-amine

Product 1

HCID 58049370N-(Tetrahydro-2H-pyran-4-yl)-N-[3-(trifluoromethoxy)benzyl]imidazo[1,2-a]pyridine-2-carboxamideYield 77.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

N-[3-(Trifluoromethoxy)benzyl]tetrahydro-2H-pyran-4-amine (242 mg), imidazo[1,2-a]pyridine-2-carboxylic acid (194 mg), EDC.HCl (199 mg), HOBt (138 mg), dimethylformamide (5 mL) and triethylamine (0.33 mL) was stirred overnight at room temperature. The solvents were distilled off under reduced pressure and following extraction with ethyl acetate, the extract was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline, and dried over anhydrous magnesium sulfate. The desiccant was filtered off and, thereafter, the solvents were concentrated. The residue was purified by column chromatography (NH silica gel cartridge; ethyl acetate) to give the titled compound (286 mg).

Workup

  1. distillationThe solvents were distilled off under reduced pressure
  2. extractionextraction with ethyl acetate
  3. washthe extract was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe desiccant was filtered off
  6. concentrationthe solvents were concentrated
  7. customThe residue was purified by column chromatography (NH silica gel cartridge; ethyl acetate)

Sources & evidence

ORD record
ord-475c298679004f1aad31a27ea279918a
Source dataset
uspto-grants-2014_01
Patent number
US08623898B2

Reaction notes

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