Hydrochloric Acid → HCID 67354233、化合物

HRID 525216ノート

反応式

HRID 525216 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][NH:12][C:13](=O)[CH2:14][C@H:15]2[CH2:19][CH2:18][N:17]([C:20]([CH:22]3[CH2:24][CH2:23]3)=[O:21])[CH2:16]2)=[O:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]([CH2:14][C@H:15]3[CH2:19][CH2:18][N:17]([C:20]([CH:22]4[CH2:24][CH2:23]4)=[O:21])[CH2:16]3)=[N:12][NH:11][C:9]2=[O:10])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 67354684HCID 67354684、化合物

生成物 1

HCID 67354233HCID 67354233、化合物収率 65%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

In a round bottom flask equipped with reflux condenser, N-(4-bromophenyl)-2-{[(3R)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]acetyl}hydrazinecarboxamide (1.896 mmol) in water (75 mL) was treated with potassium carbonate (9.48 mmol). The resulting slurry was stirred at reflux overnight (15 h). The heating was turned off and the reaction was allowed to cool to room temperature. The pH was adjusted to ˜4 using 6N aq HCl. The aqueous solution was concentrated in vacuo to ˜50 mL, which was then extracted with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography (0-10% methanol/dichloromethane). The fractions were concentrated in vacuo to provide the title compound as an off-white amorphous solid (65%). MS(ES)+ m/e 391.1, 393.2 [M+H]+.

後処理

  1. customIn a round bottom flask equipped
  2. temperaturewith reflux condenser
  3. temperatureat reflux overnight (15 h)
  4. concentrationThe aqueous solution was concentrated in vacuo to ˜50 mL, which
  5. extractionwas then extracted with ethyl acetate
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified by flash chromatography (0-10% methanol/dichloromethane)
  11. concentrationThe fractions were concentrated in vacuo

出典と根拠

ORDレコード
ord-c506550c7a5f40e6983ca3d9eab16d0f
出典データセット
uspto-grants-2016_05
特許番号
US09340529B2

反応ノート

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