Water → 3-[Bis(tert-butoxycarbonyl)aminomethyl]-6-phenylpyridazine

HRID 2359811ノート

反応式

HRID 2359811 の反応式
Br[CH2:2][C:3]1[N:4]=[N:5][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:7][CH:8]=1.[NH:15]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:26]([O:25][C:23]([N:15]([CH2:2][C:3]1[N:4]=[N:5][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:7][CH:8]=1)[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:24])([CH3:29])([CH3:28])[CH3:27]

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 279800Di-tert-butyl IminodicarboxylateHCID 667174453-(Bromomethyl)-6-phenylpyridazine

生成物 1

HCID 667177003-[Bis(tert-butoxycarbonyl)aminomethyl]-6-phenylpyridazine収率 97%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

To a solution of 3-bromomethyl-6-phenylpyridazine (120 mg, 0.482 mmol) obtained in Reference Example 2-(a) in N,N-dimethylformamide (1.57 ml) were added di-tert-butyl iminodicarboxylate (127 mg, 0.585 mmol) and potassium carbonate (134 mg, 0.970 mmol), followed by stirring at 50° C. for 2 hours. After completion of the reaction, water was added to the reaction solution, followed by extraction with ethyl acetate. The separated organic layer was dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate=2:1→1:1 (V/V)), and fractions containing the desired compound were concentrated under reduced pressure to afford the title compound (180 mg) as a slightly yellow solid. (Yield: 97%)

後処理

  1. additionwas added to the reaction solution
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe separated organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additioncontaining the desired compound
  6. concentrationwere concentrated under reduced pressure

出典と根拠

ORDレコード
ord-758a4a0eba134c9d8bef620388914d09
出典データセット
uspto-grants-2014_04
特許番号
US08685986B2

反応ノート

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