Dimethylformamide → 3-(1-{[2-Bromo-3',5'-bis(trifluoromethyl)biphenyl-4-yl]carbonyl}pyrrolidin-3-yl)pyridine

HRID 383774

반응식

HRID 383774 반응식
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][C:3]=1[C:11]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[C:13]([C:21]([F:24])([F:23])[F:22])[CH:12]=1.CCN=C=N[CH2:30][CH2:31][CH2:32][N:33]([CH3:35])C.Cl.O[N:38]1[C:42]2[CH:43]=[CH:44][CH:45]=CC=2N=N1.[CH3:47]N(C=O)C>>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([N:38]2[CH2:45][CH2:44][CH:43]([C:47]3[CH:35]=[N:33][CH:32]=[CH:31][CH:30]=3)[CH2:42]2)=[O:10])[CH:5]=[CH:4][C:3]=1[C:11]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[C:13]([C:21]([F:24])([F:23])[F:22])[CH:12]=1

참가 물질

5

반응물 4

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 866577562-Bromo-3',5'-bis(trifluoromethyl)biphenyl-4-carboxylic acid

생성물 1

HCID 866577533-(1-{[2-Bromo-3',5'-bis(trifluoromethyl)biphenyl-4-yl]carbonyl}pyrrolidin-3-yl)pyridine

실험 절차

i-5d (179 mg, 1.21 mmol) was added to a stirred solution of 3a (500 mg, 1.21 mmol), N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (255 mg, 1.33 mmol) and 1-hydroxybenzotriazole 185 mg, 1.21 mmol) in DMF (8.00 mL). After 4 h, the reaction mixture was quenched with said, aq. NaHCO3 and extracted with EtOAc. The organic layer was washed with water and brine, dried (sodium sulfate) and concentrated in vacuo. The resulting crude residue was purified by column chromatography on silica gel (gradient elution; 0%-5% methanol/EtOAc as eluent) to afford the title compound 3b. m/z (ES) 543 (MH)+.

후처리

  1. customthe reaction mixture was quenched
  2. extractionaq. NaHCO3 and extracted with EtOAc
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo
  6. customThe resulting crude residue was purified by column chromatography on silica gel (gradient elution; 0%-5% methanol/EtOAc as eluent)

출처 및 근거

ORD 기록
ord-565eb4acbea748179c320f971fd30d70
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367679B2

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