Benzoylhydrazine → HCID 59589853, compound

HRID 1054395Notes

Reaction equation

HRID 1054395 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-af0d870ca43f4fffb9a0567579985fe1
Source dataset
uspto-grants-2016_07
Patent number
US09394301B2

Reaction notes

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