Acetonitrile → 2-Acetylamino-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

HRID 2080188Notes

Reaction equation

HRID 2080188 reaction equation
[NH2:1][C:2]1[N:23]=[CH:22][CH:21]=[CH:20][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[S:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=1)=[O:5].[C:24](#N)[CH3:25].F[B-](F)(F)F.[O:32]=[N+]=O.C(=O)(O)[O-].[Na+]>O1CCCC1.C(OCC)(=O)C.O>[C:24]([NH:1][C:2]1[N:23]=[CH:22][CH:21]=[CH:20][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[S:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=1)=[O:5])(=[O:32])[CH3:25]

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 11073463Nitronium tetrafluoroborateHCID 231304232-amino-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

Product 1

HCID 231306832-Acetylamino-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamideYield 2.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-amino-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide described in Example A-67 (50 mg, 0.15 mmol), acetonitrile (5 mL) and tetrahydrofuran (2 mL) was added nitronium tetrafluoroborate (0.50M sulfolane solution, 0.46 mL, 0.23 mmol) on an ice bath, and the solution was stirred overnight at room temperature. Water, ethyl acetate, tetrahydrofuran and an aqueous solution of saturated sodium bicarbonate were added to the reaction solution for extraction, washed with brine, then, the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (methanol:ethyl acetate=1:30), and the title compound (1.3 mg, 0.0035 mmol, 2.3%) was obtained as a white solid.

Workup

  1. washwashed with brine
  2. customthe solvent was evaporated in vacuo
  3. customThe residue was purified by silica gel column chromatography (methanol:ethyl acetate=1:30)

Sources & evidence

ORD record
ord-b11ce95806314970b10bdb47a1e3c91f
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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