Methoxyacetyl chloride → 2,2-Dimethylpropyl 4-[4-(5-methoxy-1,2,4-oxadiazol-3-yl)pyridin-2-yl]-1-piperazinecarboxylate

HRID 421824ノート

反応式

HRID 421824 の反応式
[NH2:1][C:2](=[N:23][OH:24])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:16])[CH2:11][CH2:10]2)[CH:4]=1.[CH3:25][O:26][CH2:27]C(Cl)=O>N1C=CC=CC=1.C(OCC)(=O)C>[CH3:25][O:26][C:27]1[O:24][N:23]=[C:2]([C:3]2[CH:8]=[CH:7][N:6]=[C:5]([N:9]3[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:16])[CH2:11][CH2:10]3)[CH:4]=2)[N:1]=1

参加物

5

反応物 2

HCID 96623Methoxyacetyl chlorideHCID 1363817182,2-Dimethylpropyl 4-{4-[amino(hydroxyimino)methyl]pyridin-2-yl}-1-piperazinecarboxylate

生成物 1

HCID 119928012,2-Dimethylpropyl 4-[4-(5-methoxy-1,2,4-oxadiazol-3-yl)pyridin-2-yl]-1-piperazinecarboxylate

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

2,2-Dimethylpropyl 4-{4-[amino(hydroxyimino)methyl]pyridin-2-yl}piperazine-1-carboxylate (84 mg) obtained in Example 26-1) was dissolved in pyridine (2 mL), and methoxyacetyl chloride (0.035 mL) was added thereto and heated under reflux for 90 minutes. The reaction liquid was diluted with ethyl acetate, washed with 1 N hydrochloric acid, aqueous saturated sodium hydrogencarbonate solution and saturated saline water, and dried with anhydrous sodium sulfate. The solvent was evaporated away, and the resulting residue was isolated and purified through silica gel column chromatography (hexane/ethyl acetate=7/3) to obtain 54 mg of the entitled compound as a colorless oil.

後処理

  1. temperatureheated
  2. temperatureunder reflux for 90 minutes
  3. customThe reaction liquid
  4. washwashed with 1 N hydrochloric acid, aqueous saturated sodium hydrogencarbonate solution and saturated saline water
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe solvent was evaporated away
  7. customthe resulting residue was isolated
  8. custompurified through silica gel column chromatography (hexane/ethyl acetate=7/3)

出典と根拠

ORDレコード
ord-722705bd20904383a923353b668d5155
出典データセット
uspto-grants-2012_01
特許番号
US08101618B2

反応ノート

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