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Hydrazine hydrate (1:1) → 3-Pyridinecarboxylic acid, 5-[5-phenyl-4-[(2-pyridinylmethyl)amino]-2-quinazolinyl]-, hydrazide

HRID 2036812
Notes
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Reaction equation

HRID 2036812 reaction equation
[C:1]1([C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[C:9]([NH:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)=[N:10][C:11]([C:17]2[CH:18]=[N:19][CH:20]=[C:21]([CH:27]=2)[C:22]([O:24]CC)=O)=[N:12]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[NH2:37][NH2:38]>C(O)C>[C:1]1([C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[C:9]([NH:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)=[N:10][C:11]([C:17]2[CH:18]=[N:19][CH:20]=[C:21]([CH:27]=2)[C:22]([NH:37][NH2:38])=[O:24])=[N:12]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67055983HCID 67055983, compound

Product 1

HCID 670559233-Pyridinecarboxylic acid, 5-[5-phenyl-4-[(2-pyridinylmethyl)amino]-2-quinazolinyl]-, hydrazideYield 103.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl 5-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)nicotinate (Example 43) (0.2 g, 0.43 mmol) in ethanol (10 mL) was added hydrazine hydrate (0.1 mL, 2.1 mmol). The reaction mixture was heated to reflux at 80° C. for 16 h. The ethanol was evaporated under reduced pressure and the residue was dissolved in DCM and washed with water. The organic layer was dried and concentrated to provide 5-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)nicotinohydrazide (0.2 g, crude), which was used without further purification. LCMS Method E: retention time 1.8 min; [M+1]=447.50.

Workup

  1. temperatureThe reaction mixture was heated
  2. customThe ethanol was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in DCM
  4. washwashed with water
  5. customThe organic layer was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2c2752a0441949079185a6be4fbe60bf
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08575184B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes