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

HRID 2080188노트

반응식

HRID 2080188 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b11ce95806314970b10bdb47a1e3c91f
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932272B2

반응 노트

불러오는 중…