Trifluoroacetic acid → HCID 44547317, compound

HRID 1512864Notes

Reaction equation

HRID 1512864 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[N:32]([CH3:34])[CH:31]=[C:30]4[CH2:35][CH2:36][C:37]([O:39]C(C)(C)C)=[O:38])[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[N:32]([CH3:34])[CH:31]=[C:30]4[CH2:35][CH2:36][C:37]([OH:39])=[O:38])[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 67025232HCID 67025232, compound

Product 1

HCID 44547317HCID 44547317, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.475 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)-1-methyl-1H-indol-3-yl]propanoate (D10) (60 mg) in dichloromethane (1 mL) at RT. The resulting solution was stirred for 45 min. The reaction mixture was concentrated. The residue was recrystallized from ether/hexane to afford 3-[7-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]propanoic acid (E4) (40 mg) as a pale yellow solid. δH (DMSO-d6, 400 MHz): 1.39 (6H, d), 2.63 (2H, t), 2.97 (2H, t), 3.64 (3H, s), 4.99 (1H, m), 7.18 (1H, t), 7.21 (1H, s), 7.44 (1H, m), 7.57 (1H, d), 7.81 (1H, dd), 8.43 (1H, dd), 8.55 (1H, d), 12.12 (1H, br s). MS (ES): C24H22N4O4 requires 430; found 431.0 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-bdaf84fa15414c7ab3eb8fe835c599ad
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

Loading…