1,1'-Carbonyldiimidazole → HCID 59850145、化合物

HRID 2064163ノート

反応式

HRID 2064163 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 59850145HCID 59850145、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
55 °C

実験手順

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.

後処理

  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))

出典と根拠

ORDレコード
ord-dbd91615226e4a2d857ad64735f89156
出典データセット
uspto-grants-2012_10
特許番号
US08288412B2

反応ノート

読み込み中…