1,1'-Carbonyldiimidazole → HCID 59850145, 화합물

HRID 2064163노트

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HRID 2064163 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([CH3:12])=[CH:4][C:3]=1[NH:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1.C1N=CN([C:32](N2C=NC=C2)=[O:33])C=1>O1CCCC1>[CH3:12][C:5]1[C:6]([C:8]([F:11])([F:10])[F:9])=[CH:7][C:2]2[NH:1][C:32](=[O:33])[N:13]([CH:14]3[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19]3)[C:3]=2[CH:4]=1

참가 물질

4

반응물 2

HCID 682631,1'-CarbonyldiimidazoleHCID 598501931,1-Dimethylethyl 4-{[2-amino-5-methyl-4-(trifluoromethyl)phenyl]amino}-1-piperidinecarboxylate

생성물 1

HCID 59850145HCID 59850145, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
55 °C

실험 절차

1,1-Dimethylethyl 4-{[2-amino-5-methyl-4-(trifluoromethyl)phenyl]amino}-1-piperidine-carboxylate (D58) (2.92 mmol, 1.1 g) was dissolved in 5 ml of tetrahydrofuran and CDI (1,1′-(oxomethanediyl)bis-1H-imidazole) (1.5 eq., 4.4 mmol, 0.71 g) was added at room temperature; the mixture was stirred at 50-60° C. overnight. The mixture was cooled to room temperature and it was partitioned in ethyl acetate/H2O; the two layers were separated and the aqueous phase was extracted with ethyl acetate (2×); the organic phases were combined and washed with citric acid solution (10% aqueous), brine and they were dried over Na2SO4, filtered and the solvent was evaporated to afford the crude compound that was purified by chromatography (ethyl acetate-n-hexane)) to yield the title compound, 900 mg, 81%, M+−H=398.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. customit was partitioned in ethyl acetate/H2O
  3. customthe two layers were separated
  4. extractionthe aqueous phase was extracted with ethyl acetate (2×)
  5. washwashed with citric acid solution (10% aqueous), brine and they
  6. dry with materialwere dried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customto afford the crude compound that
  10. customwas purified by chromatography (ethyl acetate-n-hexane))

출처 및 근거

ORD 기록
ord-dbd91615226e4a2d857ad64735f89156
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288412B2

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