Gamma-Aminobutyric Acid → 4-[(4-{5-[2'-Methyl-2-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)amino]butanoic acid

HRID 2410608Notes

Reaction equation

HRID 2410608 reaction equation
C([BH3-])#N.[Na+].[CH3:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[O:22][N:21]=[C:20]([C:23]3[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=3)[N:19]=2)=[CH:14][C:13]=1[C:31]([F:34])([F:33])[F:32].[NH2:35][CH2:36][CH2:37][CH2:38][C:39]([OH:41])=[O:40].C(Cl)Cl>CO.C(O)(=O)C>[CH3:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[O:22][N:21]=[C:20]([C:23]3[CH:30]=[CH:29][C:26]([CH2:27][NH:35][CH2:36][CH2:37][CH2:38][C:39]([OH:41])=[O:40])=[CH:25][CH:24]=3)[N:19]=2)=[CH:14][C:13]=1[C:31]([F:34])([F:33])[F:32]

Participants

7

Reactant 4

HCID 119Gamma-Aminobutyric AcidHCID 6344DichloromethaneHCID 5003444Sodium cyanoborohydrideHCID 866615184-(5-(2'-Methyl-2-(trifluoromethyl)biphenyl-4-yl)-1,2,4-oxadiazol-3-yl)benzaldehyde

Product 1

HCID 580663044-[(4-{5-[2'-Methyl-2-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)amino]butanoic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

Sodium cyanoborohydride (18 mg, 0.28 mmol) was added to a solution of 4-(5-(2′-methyl-2-(trifluoromethyl)biphenyl-4-yl)-1,2,4-oxadiazol-3-yl)benzaldehyde (0.25 mmol) and 4-aminobutanoic acid (0.25 mmol) in a mixture of methanol (3 mL), DCM (3 mL) and acetic acid (38 μl). The mixture was stirred at room temperature overnight and was filtered through a frit under positive pressure. The solvent was removed in vacuo and the residue purified by reverse phase HPLC to give the title compound as a off-white solid. LC/MS (Method A): 494 (M−H)−, 496 (M+H)+. HPLC (Method K) Rt=17.93 min (Purity: 93.64%).

Workup

  1. filtrationwas filtered through a frit under positive pressure
  2. customThe solvent was removed in vacuo
  3. customthe residue purified by reverse phase HPLC

Sources & evidence

ORD record
ord-8b970c372883401d8129be6c4b6271ae
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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