Acetic Acid → HCID 882263, compound

HRID 1896750Notes

Reaction equation

HRID 1896750 reaction equation
[C:1]1([CH3:17])[CH:6]=[CH:5][C:4]([C:7]2[O:8][C:9]3[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][C:10]=3[N:11]=2)=[CH:3][CH:2]=1.C(O)(=O)C.[CH:22](=O)[C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.ClCCl>[N:26]1[CH:27]=[CH:28][C:23]([CH2:22][NH:16][C:13]2[CH:14]=[CH:15][C:9]3[O:8][C:7]([C:4]4[CH:3]=[CH:2][C:1]([CH3:17])=[CH:6][CH:5]=4)=[N:11][C:10]=3[CH:12]=2)=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 133894-PyridinecarboxaldehydeHCID 7218792-(4-methylphenyl)-1,3-benzoxazol-5-amineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 882263HCID 882263, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To 2-p-tolylbenzo[d]oxazol-5-amine (500 mg, 2.32 mmol) in 1,2-dichloroethane (20 mL) at room temperature was added acetic acid (142 μL, 2.32 mmol) and isonicotinaldehyde (222.5 μL, 2.29 mmol) and the mixture was stirred for 1 h. Sodium triacetoxyborohydride (707 mg, 3.35 mmol) was then added and the mixture was stirred at room temperature for 24 h. The mixture was then diluted with dichloromethane and the organic layer was washed with saturated aqueous NaHCO3. The combined organic layers were dried over anhydrous MgSO4 and evaporated. The resulting solid was purified by column chromatography eluting with ethyl acetate:hexanes 20:80 to afford 328 mg (47%) of the title compound (LCMS RT=6.27 min, MH+ 316.1)

Workup

  1. stirringthe mixture was stirred at room temperature for 24 h
  2. washthe organic layer was washed with saturated aqueous NaHCO3
  3. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  4. customevaporated
  5. customThe resulting solid was purified by column chromatography
  6. washeluting with ethyl acetate:hexanes 20:80

Sources & evidence

ORD record
ord-f871c23f58694d7fa7ad2f5f06607800
Source dataset
uspto-grants-2013_08
Patent number
US08518980B2

Reaction notes

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