Benzyl Bromide → 6-(Benzylamino)-4-{[4-chloro-3-(trifluoromethyl)benzyl]amino}quinazoline-8-carboxamide

HRID 474412Notes

Reaction equation

HRID 474412 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:9][C:10]1[CH:11]=[C:12]2[C:17](=[C:18]([C:20]([NH2:22])=[O:21])[CH:19]=1)[N:16]=[CH:15][N:14]=[C:13]2[NH:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([C:32]([F:35])([F:34])[F:33])[CH:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(Cl)Cl>[CH2:1]([NH:9][C:10]1[CH:11]=[C:12]2[C:17](=[C:18]([C:20]([NH2:22])=[O:21])[CH:19]=1)[N:16]=[CH:15][N:14]=[C:13]2[NH:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([C:32]([F:34])([F:35])[F:33])[CH:26]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 667631316-Amino-4-{[4-chloro-3-(trifluoromethyl)benzyl]amino}quinazoline-8-carboxamide

Product 1

HCID 667631366-(Benzylamino)-4-{[4-chloro-3-(trifluoromethyl)benzyl]amino}quinazoline-8-carboxamideYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

Benzylbromide (140 μL, 0.5 M in anhydrous DCM, 0.07 mmol, 1.1 equiv.) was added to a solution of 6-amino-4-{[4-chloro-3-(trifluoromethyl)benzyl]amino}quinazoline-8-carboxamide (25 mg, 0.06 mmol, 1.0 equiv.) and cesium carbonate (62 mg, 0.19 mmol, 3.0 equiv.) in anhydrous DCM (2 mL). The resulting mixture was stirred at 50° C. overnight. The title compound was obtained by pre-HPLC in 17% yield. Mass: M+H+: 486.

Sources & evidence

ORD record
ord-6f9ab4d1fda943c09e750fa04cf01e6f
Source dataset
uspto-grants-2014_01
Patent number
US08637532B2

Reaction notes

Loading…