2-Chloro-4-cyanopyridine → 4-[3-(4-Cyano-Pyridin-2-ylamino)-benzylamino]-quinazoline-8-carboxylic acid amide

HRID 474454Notes

Reaction equation

HRID 474454 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[CH2:6][NH:7][C:8]1[C:17]2[C:12](=[C:13]([C:18]([NH2:20])=[O:19])[CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][N:9]=1.Cl[C:25]1[CH:30]=[C:29]([C:31]#[N:32])[CH:28]=[CH:27][N:26]=1>CN1C(=O)CCC1>[C:31]([C:29]1[CH:28]=[CH:27][N:26]=[C:25]([NH:2][C:3]2[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=2)[CH2:6][NH:7][C:8]2[C:17]3[C:12](=[C:13]([C:18]([NH2:20])=[O:19])[CH:14]=[CH:15][CH:16]=3)[N:11]=[CH:10][N:9]=2)[CH:30]=1)#[N:32]

Participants

4

Reactant 2

HCID 5686382-Chloro-4-cyanopyridineHCID 667633584-(3-Amino-benzylamino)-quinazoline-8-carboxylic acid amide hydrochloride

Product 1

HCID 667630794-[3-(4-Cyano-Pyridin-2-ylamino)-benzylamino]-quinazoline-8-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

50 mg (0.15 mmol) 4-(3-Amino-benzylamino)-quinazoline-8-carboxylic acid amide hydrochloride and 21 mg (0.11 mmol) 2-Chloro-4-cyanopyridine were dissolved in 200 μl NMP and irradiated in the microwave at 200° C. for 3 h. The reaction mixture was directly purified using preparative HPLC. The product was treated with HCl in methanol and concentrated in the SpeedVac.

Workup

  1. customirradiated in the microwave at 200° C. for 3 h
  2. customThe reaction mixture was directly purified
  3. additionThe product was treated with HCl in methanol
  4. concentrationconcentrated in the SpeedVac

Sources & evidence

ORD record
ord-ffd302005c254ac387ec124266fb276f
Source dataset
uspto-grants-2014_01
Patent number
US08637532B2

Reaction notes

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