Trifluoroacetic acid → HCID 44129294, compound

HRID 1514291Notes

Reaction equation

HRID 1514291 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:34]=[CH:33][C:20]4[CH2:21][CH2:22][N:23](C(OC(C)(C)C)=O)[CH2:24][CH2:25][C:19]=4[CH:18]=3)[N:13]=2)[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].FC(F)(F)C(O)=O>ClCCl>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:34]=[CH:33][C:20]4[CH2:21][CH2:22][NH:23][CH2:24][CH2:25][C:19]=4[CH:18]=3)[N:13]=2)[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59403440HCID 59403440, compound

Product 1

HCID 44129294HCID 44129294, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-Dimethylethyl 7-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (Preparation 96) (305 mg, 0.629 mmol) in dichloromethane (2 mL) at room temperature was treated with trifluoroacetic acid (1 ml, 12.98 mmol) and the mixture stirred for 1 hr. The reaction mixture was concentrated and the residue partitioned between 2M NaOH and ethyl acetate. The ethyl acetate extract was washed with brine, dried and concentrated to a colourless gum which slowly crystallized, to give the title compound free base (229 mgs).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue partitioned between 2M NaOH and ethyl acetate
  3. extractionThe ethyl acetate extract
  4. washwas washed with brine
  5. customdried
  6. concentrationconcentrated to a colourless gum which
  7. customslowly crystallized

Sources & evidence

ORD record
ord-5bf1ae772bb14e71b25df0922b755d84
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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