Benzoylhydrazine → HCID 59589853, compound

HRID 1971583Notes

Reaction equation

HRID 1971583 reaction equation
P(Cl)(Cl)(Cl)=O.[N:6]1([CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]3[N:38]=[C:24]4[CH:25]=[CH:26][CH:27]=[C:28]([C:29]5[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=5)[C:32](O)=[O:33])[N:23]4[N:22]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9][CH2:8][CH2:7]1.[C:39]([NH:47][NH2:48])(=O)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.C(=O)([O-])O.[Na+]>>[C:40]1([C:39]2[O:33][C:32]([C:31]3[CH:30]=[C:29]([C:28]4[N:23]5[N:22]=[C:21]([NH:20][C:17]6[CH:16]=[CH:15][C:14]([O:13][CH2:12][CH2:11][N:6]7[CH2:10][CH2:9][CH2:8][CH2:7]7)=[CH:19][CH:18]=6)[N:38]=[C:24]5[CH:25]=[CH:26][CH:27]=4)[CH:37]=[CH:36][CH:35]=3)=[N:48][N:47]=2)[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

5

Reactant 4

HCID 11955BenzoylhydrazineHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 59589749HCID 59589749, compound

Product 1

HCID 59589853HCID 59589853, compound

Procedure

Phosphorus oxychloride (5 ml) was added dropwise to 3-{2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-5-yl}-benzoic acid (50 mg, 0.113 mmol) and benzhydrazide (15 mg, 0.113 mmol). The solution was heated to reflux overnight. Once cooled the reaction mixture was added gradually to ice/water. The solution was basified with saturated aqueous sodium hydrogencarbonate and subsequently extracted twice with dichloromethane. The organics were combined, washed several times with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The product was purified by preparatory HPLC. LCMS RT: 2.80 min, MI: 544, Method: 2.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux overnight
  3. temperatureOnce cooled the reaction mixture
  4. extractionsubsequently extracted twice with dichloromethane
  5. washwashed several times with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe product was purified by preparatory HPLC

Sources & evidence

ORD record
ord-a144333010df4fd18e0b2df15433599c
Source dataset
uspto-grants-2013_04
Patent number
US08431596B2

Reaction notes

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