Trifluoroacetic acid → HCID 21876195, compound

HRID 858478Notes

Reaction equation

HRID 858478 reaction equation
[Cl:1][C:2]1[C:7]2[N:8]=[C:9]([CH2:27][CH3:28])[N:10]([C:11]3[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][NH:19]C(=O)OC(C)(C)C)=[CH:13][CH:12]=3)[C:6]=2[CH:5]=[C:4]([CH3:29])[N:3]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[C:7]2[N:8]=[C:9]([CH2:27][CH3:28])[N:10]([C:11]3[CH:12]=[CH:13][C:14]([CH2:17][CH2:18][NH2:19])=[CH:15][CH:16]=3)[C:6]=2[CH:5]=[C:4]([CH3:29])[N:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21875678HCID 21875678, compound

Product 1

HCID 21876195HCID 21876195, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of tert-butyl 2-[4-(4-chloro-2-ethyl-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl)phenyl]ethylcarbamate (step 3, 90 mg, 0.22 mmol) in dichloromethane (8.5 ml) was added trifluoroacetic acid (1.0 ml, 13.0 mmol) at 0° C., and the mixture was stirred at 0° C. for 30 min, then at room temperature for 5 h. The mixture was concentrated, and diluted with dichloromethane (50 ml), washed with saturated aqueous NaHCO3 solution (10 ml) and brine (10 ml). The organic layer was dried (MgSO4), and concentrated. Purification by PTLC eluting with ethyl acetate to afford 50 mg (73%) of the title compound as a brown oil.

Workup

  1. waitat room temperature for 5 h
  2. concentrationThe mixture was concentrated
  3. additiondiluted with dichloromethane (50 ml)
  4. washwashed with saturated aqueous NaHCO3 solution (10 ml) and brine (10 ml)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. concentrationconcentrated
  7. customPurification by PTLC
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-eb776d7efc40402ebe29d459e35afeed
Source dataset
uspto-grants-2006_12
Patent number
US07148234B2

Reaction notes

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