Trifluoroacetic acid → HCID 22140839, compound

HRID 1826266Notes

Reaction equation

HRID 1826266 reaction equation
[Br:1][C:2]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][C:3]=1[NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[O:15][CH2:16][CH:17]2[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]2)[N:8]=[CH:7][N:6]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[Br:1][C:2]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][C:3]=1[NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[O:15][CH2:16][CH:17]2[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]2)[N:8]=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22140775HCID 22140775, compound

Product 1

HCID 22140839HCID 22140839, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(2-bromo-5-methoxyanilino)-5-[N-(tert-butoxycarbonyl)piperidin-4-ylmethoxy]quinazoline (0.108 g), trifluoroacetic acid (1 ml) and methylene chloride (1 ml) was stirred at ambient temperature for 1.5 hours. The mixture was evaporated and the residue was triturated under diethyl ether. The resultant solid was isolated and dried under vacuum. The solid was dissolved in methylene chloride and few drops of a saturated methanolic ammonia solution was added. The solution was poured onto a chromatography column filled with silica and eluted with a 97:3 mixture of methylene chloride and a saturated methanolic ammonia solution. There was thus obtained the title compound (0.082 g); NMR Spectrum: (CDCl3) 1.2–1.4 (m, 2H), 1.9 (d, 2H), 2.3 (m, 1H), 2.65 (t, 2H), 3.12 (d, 2H), 3.84 (s, 3H), 4.2 (d, 2H), 6.61 (m, 1H), 6.93 (d, 1H), 7.5 (d, 2H), 7.68 (m, 1H), 8.22 (d, 1H), 8.68 (s, 1H); Mass Spectrum: M+H+ 443 and 445.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was triturated under diethyl ether
  3. customThe resultant solid was isolated
  4. customdried under vacuum
  5. dissolutionThe solid was dissolved in methylene chloride
  6. additionfew drops of a saturated methanolic ammonia solution was added
  7. additionThe solution was poured onto a chromatography column
  8. additionfilled with silica
  9. washeluted with a 97:3 mixture of methylene chloride

Sources & evidence

ORD record
ord-93e0955829594ccf9306ca65dcd24dff
Source dataset
uspto-grants-2006_05
Patent number
US07049438B2

Reaction notes

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