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Trifluoroacetic acid → HCID 89922503, 화합물

HRID 921948
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HRID 921948 반응식
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([C:14]#[N:15])[CH:11]=[C:10]([N:16]2[CH2:28][CH2:27][C:19]3([CH2:23][N:22]([C:24](=[O:26])[CH3:25])[CH2:21][CH2:20]3)[CH2:18][CH2:17]2)[C:9]=1[Cl:29])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:24]([N:22]1[CH2:21][CH2:20][C:19]2([CH2:18][CH2:17][N:16]([C:10]3[CH:11]=[C:12]([CH:13]=[C:8]([NH2:7])[C:9]=3[Cl:29])[C:14]#[N:15])[CH2:28][CH2:27]2)[CH2:23]1)(=[O:26])[CH3:25]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 131734957HCID 131734957, 화합물

생성물 1

HCID 89922503HCID 89922503, 화합물수율 91%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

tert-butyl(3-(2-acetyl-2,8-diazaspiro[4.5]decan-8-yl)-2-chloro-5-cyanophenyl)carbamate (100 mg, 0.231 mmol) in DCM (2 mL) was treated with TFA (0.338 mL, 4.39 mmol) at room temperature for 2 h. Solvent was evaporated and the residue was diluted with dichloromethane and washed with saturated sodium bicarbonate. The aqueous layer was extracted with dichloromethane two more times. The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo, the crude product was purified by flash chromatography on silica gel using an automated ISCO system (24 g gold column, eluting with 0-5% methanol/dichloromethane). 3-(2-acetyl-2,8-diazaspiro[4.5]decan-8-yl)-5-amino-4-chlorobenzonitrile (70 mg) was obtained as a light yellow oil.

후처리

  1. customSolvent was evaporated
  2. additionthe residue was diluted with dichloromethane
  3. washwashed with saturated sodium bicarbonate
  4. extractionThe aqueous layer was extracted with dichloromethane two more times
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customthe crude product was purified by flash chromatography on silica gel using
  9. washan automated ISCO system (24 g gold column, eluting with 0-5% methanol/dichloromethane)

출처 및 근거

ORD 기록
ord-b290bd4ec0b346e9a154445703edf776
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09273057B2

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