Trifluoroacetic acid → HCID 69035589, compound

HRID 1782073Notes

Reaction equation

HRID 1782073 reaction equation
C(OC([NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:29]=[C:28]3[C:23]([C:24]([NH:30][C:31]([NH:33][C:34]4[C:39]([Cl:40])=[CH:38][CH:37]=[CH:36][C:35]=4[Cl:41])=[O:32])=[N:25][CH:26]=[N:27]3)=[CH:22][C:21]=2[O:42][CH3:43])[CH2:12][CH2:11]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[NH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:29]=[C:28]3[C:23]([C:24]([NH:30][C:31]([NH:33][C:34]4[C:35]([Cl:41])=[CH:36][CH:37]=[CH:38][C:39]=4[Cl:40])=[O:32])=[N:25][CH:26]=[N:27]3)=[CH:22][C:21]=2[O:42][CH3:43])[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22649300HCID 22649300, compound

Product 1

HCID 69035589HCID 69035589, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 1-{7-[3-(4-tert-butoxycarbonylaminomethylpiperidin-1-yl)propoxy]-6-methoxyquinazolin-4-yl}-3-(2,6-dichlorophenyl)urea (0.075 g), trifluoroacetic acid (0.35 ml) and chloroform (1.5 ml) was stirred at ambient temperature for 40 minutes. The mixture was evaporated and the residue was stirred under a 1N aqueous sodium hydroxide solution (3 ml) for 1 hour. The resultant solid was isolated and dried. There was thus obtained the title compound (0.037 g); NMR Spectrum: (DMSOd6) 1:12 (m, 3H), 1.62-1.7 (m, 2H), 1.9 (t, 2H), 2.0 (m, 4H), 2.38-2.54 (m, 4H), 2.92 (m, 2H), 3.3 (m, partially obscured by a water signal), 3.95 (s, 3H), 4.26 (t, 2H), 7.28 (s, 1H), 7.41 (t, 1H), 7.62 (d, 2H), 8.06 (s, 1H), 8.66 (s, 1H); Mass Spectrum: M+H+ 533 and 535.

Workup

  1. customThe mixture was evaporated
  2. stirringthe residue was stirred under a 1N aqueous sodium hydroxide solution (3 ml) for 1 hour
  3. customThe resultant solid was isolated
  4. customdried

Sources & evidence

ORD record
ord-5236f07c1de741cbac7db4b973b3770a
Source dataset
uspto-grants-2009_03
Patent number
US07498335B2

Reaction notes

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