Acetic Acid → HCID 59556755, compound

HRID 1172986Notes

Reaction equation

HRID 1172986 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[N:16]=[C:15]([C:17]3[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=3)[O:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].O=[C:25]1[CH2:28][CH:27]([C:29]([OH:31])=[O:30])[CH2:26]1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[N:16]=[C:15]([C:17]3[CH:18]=[CH:19][C:20]([NH:21][CH:25]4[CH2:28][CH:27]([C:29]([OH:31])=[O:30])[CH2:26]4)=[CH:22][CH:23]=3)[O:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 49133583-Oxocyclobutane-1-carboxylic acidHCID 5003444Sodium cyanoborohydrideHCID 59556548HCID 59556548, compound

Product 1

HCID 59556755HCID 59556755, compoundYield 56.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)aniline (250 mg, 0.531 mmol) in Methanol (1478 μl) at room temperature was added 3-oxocyclobutanecarboxylic acid (60.5 mg, 0.531 mmol) followed by acetic acid (814 μl, 14.22 mmol). The reaction mixture was stirred at room temperature for 5 minutes before the addition of sodium cyanoborohydride (16.67 mg, 0.265 mmol). The reaction mixture was stirred overnight at room temperature. The solvent was removed and the crude material purified by FCC (50% ethyl acetate/heptane) to afford 3-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenylamino)cyclobutanecarboxylic acid (139 mg, 0.302 mmol, 56.9% yield) as a white solid. LCMS (Table A, Method b) 2.89 min, (M+H)+ 428.20.

Workup

  1. customThe solvent was removed
  2. customthe crude material purified by FCC (50% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-ebb392ca977041d8827c9d2dd2603444
Source dataset
uspto-grants-2010_11
Patent number
US07834039B2

Reaction notes

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