Acetic Acid → HCID 24780524, compound

HRID 2241806Notes

Reaction equation

HRID 2241806 reaction equation
O[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[NH:10][C:11](=[O:20])[C:12]1[CH:17]=[CH:16][C:15]([NH:18][CH3:19])=[N:14][CH:13]=1.[C:21](O)(=[O:23])[CH3:22].C(=O)(O)[O-].[Na+]>O>[CH3:9][O:8][C:6]1[CH:5]=[CH:4][C:3]2[N:10]=[C:11]([C:12]3[CH:17]=[CH:16][C:15]([N:18]([CH3:19])[C:21](=[O:23])[CH3:22])=[N:14][CH:13]=3)[O:20][C:2]=2[CH:7]=1.[CH3:9][O:8][C:6]1[CH:5]=[CH:4][C:3]2[N:10]=[C:11]([C:12]3[CH:17]=[CH:16][C:15]([NH:18][CH3:19])=[N:14][CH:13]=3)[O:20][C:2]=2[CH:7]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 59203854HCID 59203854, compound

Product 2

HCID 24780524HCID 24780524, compoundHCID 24780654HCID 24780654, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-(2-Hydroxy-4-methoxyphenyl)-6-(methylamino)nicotinamide (0.23 g, 0.84 mmol) was mixed with acetic acid (4 mL) and the reaction was run in a microwave reactor at 200° C. for 25 minutes. The reaction mixture was added to water and made basic with sodium bicarbonate (sat. aq.). The aqueous solution was extracted three times with diethyl ether and the combined organic layers were washed with brine, dried (MgSO4) and evaporated. The crude product was purified first by flash column chromatography (hexane/ethyl acetate-gradient; 30-50% ethyl acetate), followed by preparative HPLC, resulting in the isolation of N-[5-(6-methoxy-1,3-benzoxazol-2-yl)pyridin-2-yl]-N-methylacetamide (6 mg) as a minor product, together with the title compound (0.13 g) as a solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.90 (d, 1H) 8.23 (dd, 1H) 7.59 (d, 1H) 7.10 (d, 1H) 6.94 (dd, 1H) 6.52 (d, 1H) 5.26 (br. s, 1H) 3.89 (s, 3H) 2.82-3.16 (m, 3 H); MS m/z (M+H) 256.

Workup

  1. extractionThe aqueous solution was extracted three times with diethyl ether
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe crude product was purified first by flash column chromatography (hexane/ethyl acetate-gradient; 30-50% ethyl acetate)

Sources & evidence

ORD record
ord-90beea9831ab428ca9145dde2751b65d
Source dataset
uspto-grants-2010_03
Patent number
US07670591B2

Reaction notes

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