4-Cyanophenyl isocyanate → HCID 22291147, compound

HRID 967721Notes

Reaction equation

HRID 967721 reaction equation
[N:1]1([C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH2:18][CH2:19][CH:20]4[CH2:25][CH2:24][CH2:23][CH2:22][NH:21]4)=[CH:14][CH:15]=3)[N:10]=[CH:9][N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:26]([C:28]1[CH:33]=[CH:32][C:31]([N:34]=[C:35]=[O:36])=[CH:30][CH:29]=1)#[N:27]>CN(C=O)C>[C:26]([C:28]1[CH:29]=[CH:30][C:31]([NH:34][C:35]([N:4]2[CH2:3][CH2:2][N:1]([C:7]3[C:16]4[C:11](=[CH:12][C:13]([O:17][CH2:18][CH2:19][CH:20]5[CH2:25][CH2:24][CH2:23][CH2:22][NH:21]5)=[CH:14][CH:15]=4)[N:10]=[CH:9][N:8]=3)[CH2:6][CH2:5]2)=[O:36])=[CH:32][CH:33]=1)#[N:27]

Participants

4

Reactant 2

HCID 1703804-Cyanophenyl isocyanateHCID 68614207HCID 68614207, compound

Product 1

HCID 22291147HCID 22291147, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To DMF solution (2 mL) of 4-piperazinyl-7-(2-piperidylethoxy)quinazoline (from Example 1, Step E, 0.287 g, 0.84 mmol) added DMF solution (2 mL) of 4-cyanophenylisocyanate (0.181 g, 1.26 mmol) and the reaction was stirred at room temperature overnight. The solvent was evaporated and residue purified by RP-EHLC to afford desired product N-(4-cyanophenyl){4-[7-(2-piperidylethoxy)quinazolin-4-yl]piperazinyl}carboxamide as a white solid (200 mg, 50%). MS (ES) 487(M+H)

Workup

  1. customThe solvent was evaporated
  2. customresidue purified by RP-EHLC

Sources & evidence

ORD record
ord-e0d64325055d42d6b967b6f85273fd52
Source dataset
uspto-grants-2005_10
Patent number
US06956039B2

Reaction notes

Loading…