Trifluoroacetic acid → HCID 59146155, compound

HRID 1512765Notes

Reaction equation

HRID 1512765 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:25]=3[NH:24][CH:23]=[C:22]4[C:26](=O)[CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].C(O)(C(F)(F)F)=O.C([BH3-])#N.[Na+]>C(O)C.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:25]=3[NH:24][CH:23]=[C:22]4[CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 5003444Sodium cyanoborohydrideHCID 59146159ethyl 4-{7-[5-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl]-1H-indol-3-yl}-4-oxobutanoate

Product 1

HCID 59146155HCID 59146155, compoundYield 51.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

To a solution of ethyl 4-{7-[5-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl]-1H-indol-3-yl}-4-oxobutanoate (D52) (300 mg) and TFA (5 mL) in ethanol (15 mL) and DCM (15 mL) was added sodium cyanoborohydride (235 mg) in portions. The reaction mixture was stirred at 20° C. for 4 days. The mixture was diluted with DCM (30 mL) and washed with water. The organic phase was separated and dried over anhydrous sulphate. After filtration, the solvent was evaporated to give the crude product, which was purified by preparative TLC separation to afford ethyl 4-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]butanoate (D53) as a white solid (150 mg). MS (ES): C25H26ClN3O4 requires 467; found 468.2 (M+H+).

Workup

  1. washwashed with water
  2. customThe organic phase was separated
  3. dry with materialdried over anhydrous sulphate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated
  6. customto give the crude product, which
  7. customwas purified by preparative TLC separation

Sources & evidence

ORD record
ord-c96a6c5a025a4e719ba4450848d90089
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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