Trifluoroacetic acid → HCID 44517833, compound

HRID 1512863Notes

Reaction equation

HRID 1512863 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:26]=[CH:27][CH:28]=[C:29]4[C:33]=3[NH:32][CH:31]=[C:30]4[CH2:34][CH2:35][C:36]([O:38]C(C)(C)C)=[O:37])[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:26]=[CH:27][CH:28]=[C:29]4[C:33]=3[NH:32][CH:31]=[C:30]4[CH2:34][CH2:35][C:36]([OH:38])=[O:37])[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 67094388HCID 67094388, compound

Product 1

HCID 44517833HCID 44517833, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.37 mL) was added to a solution of 1,1-dimethylethyl 3-[7-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propanoate (D9) (45 mg) in dichloromethane (0.5 mL) at RT. The resulting solution was stirred for 2 hours. The reaction mixture was concentrated. The residue was recrystallized from dichloromethane to afford 3-[7-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propanoic acid (E3) (27 mg) as a white solid. δH (DMSO-d6, 400 MHz): 1.40 (6H, d), 2.67 (2H, t), 3.03 (2H, t), 5.01 (1H, m), 7.22 (1H, t), 7.28 (1H, d), 7.46 (1H, d), 7.83 (1H, d), 7.95 (1H, dd), 8.21 (1H, dd), 8.39 (1H, d), 10.86 (1H, s), 12.12 (1H, br s). MS (ES): C23H20N4O4 requires 416; found 417.1 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-82061b515585426882f73cf381e509a4
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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