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

HRID 578689Notes

Reaction equation

HRID 578689 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 irridiated 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. customThe reaction mixture was directly purified
  2. additionThe product was treated with HCl in methanol
  3. concentrationconcentrated in the SpeedVac

Sources & evidence

ORD record
ord-13e4d0640fd54874a7d08030ea0829bd
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

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