Phenyl isocyanate → 2-Amino-4-(1-phenylcarbamoyl-4-piperidinyl)quinazoline

HRID 617182Notes

Reaction equation

HRID 617182 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(N(CC)CC)C.[C:25]1([N:31]=[C:32]=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>ClCCl>[NH2:1][C:2]1[N:11]=[C:10]([CH:12]2[CH2:17][CH2:16][N:15]([C:32](=[O:33])[NH:31][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 154287752-Amino-4-(4-piperidinyl)quinazoline

Product 1

HCID 218515192-Amino-4-(1-phenylcarbamoyl-4-piperidinyl)quinazolineYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-4-(4-piperidinyl)quinazoline (100 mg, 0.44 mmol) obtained in Example 11(1) and triethylamine (133 mg, 1.3 mmol) in dichloromethane (50 ml) was added phenyl isocyanate (50 mg, 0.42 mmol) under a nitrogen atmosphere. The mixture was stirred for about 3 hours at room temperature. The reaction mixture was washed with saturated sodium hydrogencarbonate aqueous solution. The organic layer was dried over sodium sulfate and evaporated in vacuo. The residue was purified by silicagel column chromatography (chloroform:methanol=99:1) to give the titled compound (127 mg).

Workup

  1. washThe reaction mixture was washed with saturated sodium hydrogencarbonate aqueous solution
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by silicagel column chromatography (chloroform:methanol=99:1)

Sources & evidence

ORD record
ord-91c7730f43df421a9a14133717031f4a
Source dataset
uspto-grants-1999_09
Patent number
US05948786

Reaction notes

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