Trifluoroacetic acid → HCID 178505566, compound

HRID 2116904Notes

Reaction equation

HRID 2116904 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[NH:15][C:16]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)=[C:17]([Cl:19])[N:18]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[C:27]([OH:33])([C:29]([F:32])([F:31])[F:30])=[O:28]>C(Cl)Cl>[F:30][C:29]([F:32])([F:31])[C:27]([OH:33])=[O:28].[Cl:19][C:17]1[N:18]=[C:14]([C:11]2[CH2:10][CH2:9][N:8]([C:6]3[C:27]([C:29]([F:32])([F:31])[F:30])=[CH:11][CH:10]=[CH:9][N:8]=3)[CH2:13][CH:12]=2)[NH:15][C:16]=1[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178451803HCID 178451803, compound

Product 1

HCID 178505566HCID 178505566, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-[4-chloro-5-(4-fluoro-phenyl)-1H-imidazol-2-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester from step (b) above in 30% TFA in DCM (5 mL) was stirred at RT for 1 h. The solvents were removed, and the residue was stirred with sat. aqueous solution of NaHCO3 (10 mL) at RT for 0.5 h. The reaction mixture was extracted with EtOAc (2×10 mL). The combined organic extracts were dried over MgSO4 and filtered. The filtrate was evaporated in vacuo to give the title compound, which was directly used in the next step without additional purification. MS (ESI, positive ion) m/z: 278 (M+1).

Workup

  1. customThe solvents were removed
  2. extractionThe reaction mixture was extracted with EtOAc (2×10 mL)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-c0160ac1d83d4ad9b7467c8eceebbf7a
Source dataset
uspto-grants-2008_10
Patent number
US07439360B2

Reaction notes

Loading…