Trifluoroacetic acid → HCID 44547459, compound

HRID 1512867Notes

Reaction equation

HRID 1512867 reaction equation
FC(F)(F)C(O)=O.[C:8]([C:10]1[CH:11]=[C:12]([C:20]2[O:24][N:23]=[C:22]([C:25]3[CH:33]=[C:32]4[C:28]([C:29]([CH2:34][CH2:35][C:36]([O:38]C(C)(C)C)=[O:37])=[CH:30][NH:31]4)=[CH:27][CH:26]=3)[N:21]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH:17]([CH3:19])[CH3:18])#[N:9]>ClCCl>[C:8]([C:10]1[CH:11]=[C:12]([C:20]2[O:24][N:23]=[C:22]([C:25]3[CH:33]=[C:32]4[C:28]([C:29]([CH2:34][CH2:35][C:36]([OH:38])=[O:37])=[CH:30][NH:31]4)=[CH:27][CH:26]=3)[N:21]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH:17]([CH3:19])[CH3:18])#[N:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67025190HCID 67025190, compound

Product 1

HCID 44547459HCID 44547459, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.856 mL) was added to a solution of 1,1-dimethylethyl 3-[6-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propanoate (D19) (105 mg) in dichloromethane (1.5 mL) at RT. The resulting solution was stirred for 1.5 hours. The reaction mixture was concentrated. The residue was recrystallized from dichloromethane/ether to afford 3-[6-(5-{3-Cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propanoic acid (E7) (69 mg) as a white solid. δH (DMSO-d6, 400 MHz): 1.39 (6H, d), 2.65 (2H, t), 2.97 (2H, t), 4.98 (1H, m), 7.36 (1H, d), 7.56 (1H, d), 7.72 (2H, t), 8.12 (1H, s), 8.42 (1H, dd), 8.51 (1H, d), 11.22 (1H, s), 12.12 (1H, br s). MS (ES): C23H20N4O4 requires 416. found 416.9 (M+H+).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe residue was recrystallized from dichloromethane/ether

Sources & evidence

ORD record
ord-594ca9f804e744bd957646ec4916cd81
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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