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

HRID 2080188ノート

反応式

HRID 2080188 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-b11ce95806314970b10bdb47a1e3c91f
出典データセット
uspto-grants-2011_04
特許番号
US07932272B2

反応ノート

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