Ammonia → HCID 70921718、化合物

HRID 2069134ノート

反応式

HRID 2069134 の反応式
[CH3:1][C:2]1[C:15]([CH3:16])=[C:14]([N+:17]([O-:19])=[O:18])[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH2:11])[CH:6]=1.CCN(C(C)C)C(C)C.[CH3:29][O:30][CH2:31][C:32](Cl)=[O:33].N>C1COCC1.CO>[CH3:1][C:2]1[C:15]([CH3:16])=[C:14]([N+:17]([O-:19])=[O:18])[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:32](=[O:33])[CH2:31][O:30][CH3:29])[CH:6]=1

参加物

7

反応物 4

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 96623Methoxyacetyl chlorideHCID 585648204-(2,3-Dimethyl-4-nitrophenoxy)pyridin-2-amine

生成物 1

HCID 70921718HCID 70921718、化合物収率 67%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of 4-(2,3-dimethyl-4-nitrophenoxy)pyridin-2-amine (110 mg, 0.424 mmol) in THF (3.0 mL) containing DIPEA (370 μL, 2.12 mmol) at 0° C. was added 2-methoxyacetyl chloride (155 μL, 1.70 mmol) in a single portion. The reaction mixture was warmed to RT for 1 hr and a solution of NH3 in MeOH (7M, 2.0 mL) was added and the resulting mixture maintained at RT for 16 hr and then evaporated in vacuo. The residue was partitioned between DCM (50 mL) and brine (40 mL) and the organic phase was seprated and dried (MgSO4) and was evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 40 g, 20-50% EtOAc in isohexane, gradient elution) to afford N-(4-(2,3-dimethyl-4-nitrophenoxy)pyridin-2-yl)-2-methoxyacetamide (94 mg, 67%) as an orange oil; Rt 2.14 min (Method 2); m/z 332 (M+H)+ (ES+).

後処理

  1. temperaturethe resulting mixture maintained at RT for 16 hr
  2. customevaporated in vacuo
  3. customThe residue was partitioned between DCM (50 mL) and brine (40 mL)
  4. dry with materialdried (MgSO4)
  5. customwas evaporated in vacuo
  6. customThe residue was purified by flash column chromatography (SiO2, 40 g, 20-50% EtOAc in isohexane, gradient elution)

出典と根拠

ORDレコード
ord-aed2d25226024b81a063ca8fd3341b73
出典データセット
uspto-grants-2012_10
特許番号
US08299074B2

反応ノート

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