Acetic Anhydride → Acetamide,n-[4-(6-amino-4-methyl-2-pyridinyl)butyl]-

HRID 1740960ノート

反応式

HRID 1740960 の反応式
C(N(CC)CC)C.C(O[C:12](=[O:14])[CH3:13])(=O)C.[NH2:15][C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH2:23][CH2:24][CH2:25][CH2:26][NH2:27])[N:17]=1>ClCCl.C(OCC)(=O)C>[C:12]([NH:27][CH2:26][CH2:25][CH2:24][CH2:23][C:18]1[N:17]=[C:16]([NH2:15])[CH:21]=[C:20]([CH3:22])[CH:19]=1)(=[O:14])[CH3:13]

参加物

6

反応物 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 98556396-amino-4-methyl-2-Pyridinebutanamine

生成物 1

HCID 9855950Acetamide,n-[4-(6-amino-4-methyl-2-pyridinyl)butyl]-収率 44%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Triethylamine (0.059 mL, 43 mg, 0.42 mmol) and acetic anhydride (0.029 mL, 31 mg, 0.031 mmol) were added to a solution of 50 mg (0.028 mmol) of 2-amino-6-(4-aminobutyl)-4-methylpyridine (from Example 56) in 1.0 mL of dichloromethane. The solution was allowed to stand for 48 h at room temperature, then diluted with 25 mL of ethyl acetate and washed with 12 mL of saturated aqueous sodium bicarbonate and 12 mL of saturated aqueous sodium chloride. The aqueous layers were extracted in succession with 15 mL of ethyl acetate. The combined organic layers were dried (sodium sulfate), decanted, and evaporated. The residue was purified by flash column chromatography on 3.5 g of silica gel, eluting with 100 mL of 5% methanol in dichloromethane to give 27 mg (44% yield of 6-(4-acetamidobutyl)-2-amino-4-methylpyridine as an oil which spontaneously crystallized.

後処理

  1. washwashed with 12 mL of saturated aqueous sodium bicarbonate and 12 mL of saturated aqueous sodium chloride
  2. extractionThe aqueous layers were extracted in succession with 15 mL of ethyl acetate
  3. dry with materialThe combined organic layers were dried (sodium sulfate)
  4. customdecanted
  5. customevaporated
  6. customThe residue was purified by flash column chromatography on 3.5 g of silica gel
  7. washeluting with 100 mL of 5% methanol in dichloromethane

出典と根拠

ORDレコード
ord-c7b7deb998d144f18d3838545356dc5f
出典データセット
uspto-grants-1999_10
特許番号
US05972975

反応ノート

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