Trifluoroacetic acid → 1-(2,6-Dichlorophenyl)-3-[6-methoxy-7-(6-methylamino-1-hexynyl)quinazolin-4-yl]urea

HRID 393246Notes

Reaction equation

HRID 393246 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]([NH:12][C:13]1[C:22]2[C:17](=[CH:18][C:19]([C:25]#[C:26][CH2:27][CH2:28][CH2:29][CH2:30][N:31](NC(OC(C)(C)C)=O)[CH3:32])=[C:20]([O:23][CH3:24])[CH:21]=2)[N:16]=[CH:15][N:14]=1)=[O:11].FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]([NH:12][C:13]1[C:22]2[C:17](=[CH:18][C:19]([C:25]#[C:26][CH2:27][CH2:28][CH2:29][CH2:30][NH:31][CH3:32])=[C:20]([O:23][CH3:24])[CH:21]=2)[N:16]=[CH:15][N:14]=1)=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 226492701-(2,6-dichlorophenyl)-3-{7-[6-(N-tert-butoxycarbonylamino-N-methylamino)-1-hexynyl]-6-methoxyquinazolin-4-yl}urea

Product 1

HCID 226493301-(2,6-Dichlorophenyl)-3-[6-methoxy-7-(6-methylamino-1-hexynyl)quinazolin-4-yl]urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(2,6-dichlorophenyl)-3-{7-[6-(N-tert-butoxycarbonylamino-N-methylamino)-1-hexynyl]-6-methoxyquinazolin-4-yl}urea (0.1 g), trifluoroacetic acid (1 ml) and methylene chloride (1 ml) was stirred at ambient temperature for 1.5 hours. The mixture was evaporated and a solution of hydrogen chloride gas in ethyl acetate was added. Toluene was added and the mixture was evaporated. The residue was triturated under diethyl ether and the resultant solid was isolated. There was thus obtained the title compound as the hydrochloride salt (0.095 g); NMR Spectrum: (DMSOd6) 1.65 (m, 2H), 1.78 (m, 2H), 2.55 (m, 5H), 2.95 (m, 2H), 4.0 (s, 3H), 7.38 (t, 1H), 7.6 (d, 2H), 7.89 (s, 1H), 8.16 (s, 1H), 8.7 (m, 3H), 10.9 (br, 1H), 11.8 (s, 1H); Mass Spectrum: M+H+ 472 and 474.

Workup

  1. customThe mixture was evaporated
  2. additiona solution of hydrogen chloride gas in ethyl acetate was added
  3. additionToluene was added
  4. customthe mixture was evaporated
  5. customThe residue was triturated under diethyl ether
  6. customthe resultant solid was isolated

Sources & evidence

ORD record
ord-292f1246fbbb4c0eae6c87d77ea770cb
Source dataset
uspto-grants-2004_10
Patent number
US06806274B1

Reaction notes

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