Acetic Acid → HCID 59556762, compound

HRID 1172984Notes

Reaction equation

HRID 1172984 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[C:9]1[O:13][N:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH:21]([CH3:23])[CH3:22])=[C:16]([Cl:24])[CH:15]=2)[N:10]=1)[NH2:5].O=[C:26]1[CH2:29][CH:28]([C:30]([OH:32])=[O:31])[CH2:27]1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][CH:26]2[CH2:29][CH:28]([C:30]([OH:32])=[O:31])[CH2:27]2)[CH:6]=[CH:7][C:8]=1[C:9]1[O:13][N:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH:21]([CH3:22])[CH3:23])=[C:16]([Cl:24])[CH:15]=2)[N:10]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 49133583-Oxocyclobutane-1-carboxylic acidHCID 5003444Sodium cyanoborohydrideHCID 59556614HCID 59556614, compound

Product 1

HCID 59556762HCID 59556762, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-chloro-4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)aniline (200 mg, 0.549 mmol) and 3-oxocyclobutanecarboxylic acid (62.7 mg, 0.549 mmol) in methanol (1280 μl) at room temperature was added acetic acid (842 μl, 14.72 mmol). The reaction mixture was stirred at room temperature for 10 minutes before addition of sodium cyanoborohydride (17.25 mg, 0.275 mmol) as a single portion. The reaction mixture was stirred at room temperature overnight. LCMS (2007—9476) indicated a 43% by ELSD (2.90 min)s conversion to (M+H) 462.16. The solvent was removed and the crude material purified by FCC (50% EA/Hept) to afford 3-(3-chloro-4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenylamino)cyclobutanecarboxylic acid (135 mg, 0.292 mmol, 53.2% yield) as a white solid. LCMS (Table A, Method b) indicated 100% by UV (3.06 mins) to (M+H)+ 364.12.

Workup

  1. customby ELSD (2.90 min)
  2. customThe solvent was removed
  3. customthe crude material purified by FCC (50% EA/Hept)

Sources & evidence

ORD record
ord-41f45146e437485990439f3d08261341
Source dataset
uspto-grants-2010_11
Patent number
US07834039B2

Reaction notes

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