Hydrochloric Acid → HCID 67354233, 화합물

HRID 2405400노트

반응식

HRID 2405400 반응식
[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

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 67354684HCID 67354684, 화합물

생성물 1

HCID 67354233HCID 67354233, 화합물수율 65%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-337472768de14733bf34a3fbdd427c11
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08802864B2

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