Hydrazine → HCID 178474055, compound

HRID 537041Notes

Reaction equation

HRID 537041 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[O:12][C:13]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])=[C:14]([C:16]([NH2:18])=O)[N:15]=2)[C:8]([CH3:26])=[CH:7][N:6]=1)(=[O:3])[CH3:2].C[N:28]([CH:30](OC)OC)C.[NH2:35]N.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[Cl:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:13]1[O:12][C:11]([C:9]2[C:8]([CH3:26])=[CH:7][N:6]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:10]=2)=[N:15][C:14]=1[C:16]1[NH:18][CH:30]=[N:28][N:35]=1

Participants

6

Reactant 4

HCID 9321HydrazineHCID 78373Dimethylformamide dimethyl acetalHCID 516892Sodium BicarbonateHCID 56839570HCID 56839570, compound

Product 1

HCID 178474055HCID 178474055, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 2-[2-(acetylamino)-5-methylpyridin-4-yl]-5-(2-chlorophenyl)-1,3-oxazole-4-carboxamide (0.48 g, 1.3 mmol) in dry toluene (7 mL) was sonicated for 15 min. DMF-DMA (0.51 mL, 3.8 mmol) was added and the mixture was allowed to stir at 50° C. for 2 h. The suspension was cooled to rt and was concentrated. The resulting solid was suspended in AcOH (5 mL) at rt. Hydrazine (0.20 mL, 6.4 mmol) was added dropwise. The reaction mixture was allowed to stir at 40° C. for 3 h. Saturated NaHCO3 was added until the mixture became neutral. The solid was filtered, washed with water, and purified by column chromatography to give N-{4-[5-(2-chlorophenyl)-4-(4H-1,2,4-triazol-3-yl)-1,3-oxazol-2-yl]-5-methylpyridin-2-yl}acetamide (0.23 g, 45%). LCMS (FA): m/z=395.3 (M+H).

Workup

  1. customwas sonicated for 15 min
  2. temperatureThe suspension was cooled to rt
  3. concentrationwas concentrated
  4. customwas suspended in AcOH (5 mL) at rt
  5. stirringto stir at 40° C. for 3 h
  6. filtrationThe solid was filtered
  7. washwashed with water
  8. custompurified by column chromatography

Sources & evidence

ORD record
ord-f1447045ece54a8dab4c6a5120a15e99
Source dataset
uspto-grants-2014_10
Patent number
US08859768B2

Reaction notes

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