2-Chloro-N,N-dimethylquinazolin-4-amine → HCID 178483097, compound

HRID 1984943Notes

Reaction equation

HRID 1984943 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:13]=2[O:19][C:20]([F:23])([F:22])[F:21])(=[O:11])=[O:10])[CH2:4][CH2:3]1.Cl[C:25]1[N:34]=[C:33]([N:35]([CH3:37])[CH3:36])[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:26]=1>CC(O)C>[Br:18][C:15]1[CH:16]=[CH:17][C:12]([S:9]([NH:8][C@H:5]2[CH2:6][CH2:7][C@H:2]([NH:1][C:25]3[N:34]=[C:33]([N:35]([CH3:37])[CH3:36])[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:26]=3)[CH2:3][CH2:4]2)(=[O:11])=[O:10])=[C:13]([O:19][C:20]([F:22])([F:23])[F:21])[CH:14]=1

Participants

4

Reactant 2

HCID 126843422-Chloro-N,N-dimethylquinazolin-4-amineHCID 178511687HCID 178511687, compound

Product 1

HCID 178483097HCID 178483097, compoundYield 295.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of trans-N-(4-amino-cyclohexyl)-4-bromo-2-trifluoromethoxy-benzenesulfonamide (100 mg, 0.24 mmol) in 2-propanol (0.5 mL) was added (2-chloro-quinazolin-4-yl)-dimethly-amine obtained in step B of example 1 (54.7 mg, 0.26 mmol). The mixture was heated using a Smith Microwave Synthesizer at 170° C. for 15 min. The mixture was concentrated and the residue was purified by chromatography (2% to 4% 2 M NH3/MeOH in CH2Cl2) to give trans-4-bromo-N-[4-(4-dimethlyamino-quinazolin-2-ylamino)-cyclohexyl]-2-trifluoromethoxy-benzenesulfonamide (42 mg, 0.71 mmol, 30%) as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. customat 170° C.
  3. customfor 15 min
  4. concentrationThe mixture was concentrated
  5. customthe residue was purified by chromatography (2% to 4% 2 M NH3/MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-cc5e83cb537d4f9c874db9bd37a61444
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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