Ammonia → HCID 135510694, compound

HRID 1373305Notes

Reaction equation

HRID 1373305 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:19][C:20]3[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=3[Cl:28])=[N:14][CH:15]=[N:16]2)=[C:11]([O:29][CH:30]2[CH2:34][CH2:33][O:32][CH2:31]2)[CH:10]=1)C1C=CC=CC=1.FC(F)(F)C(O)=O.N>C(Cl)Cl>[Cl:28][C:21]1[CH:22]=[CH:23][C:24]([O:26][CH3:27])=[CH:25][C:20]=1[NH:19][C:13]1[C:12]2[C:17](=[CH:18][C:9]([OH:8])=[CH:10][C:11]=2[O:29][CH:30]2[CH2:34][CH2:33][O:32][CH2:31]2)[N:16]=[CH:15][N:14]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 11974942HCID 11974942, compound

Product 1

HCID 135510694HCID 135510694, compoundYield 148.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using an analogous procedure to that described in Example 20, 7-benzyloxy-4-(2-chloro-5-methoxyanilino)-5-tetrahydrofuran-3-yloxyquinazoline (0.39 g) was reacted with trifluoroacetic acid (2.5 ml). The reaction mixture was evaporated and the residue was triturated under diethyl ether. The precipitate was isolated and the solid was dissolved in a mixture of methylene chloride and a saturated methanolic ammonia solution. The mixture was evaporated and the residue was purified by column chromatography on silica using a 97:3 mixture of methylene chloride and methanol as eluent. There was thus obtained the title compound (0.47 g); NMR Spectrum: (DMSOd6 and CF3CO2D) 2.2–2.3 (m, 1H), 2.3–2.5 (m, 1H), 3.8 (s, 3H), 3.75–3.9 (m, 1H), 3.9–4.0 (m, 2H), 4.2 (d, 1H), 5.5 (m, 1H), 6.8 (s, 1H), 6.92 (s, 1H), 7.02 (m, 1H), 7.55 (d, 1H), 7.6 (d, 1H), 8.85 (s, 1H); Mass Spectrum: M+H+ 388 and 390.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was triturated under diethyl ether
  3. customThe precipitate was isolated
  4. customThe mixture was evaporated
  5. customthe residue was purified by column chromatography on silica using
  6. additiona 97:3 mixture of methylene chloride and methanol as eluent

Sources & evidence

ORD record
ord-f5924db7226048e3b50c8c2ea3827802
Source dataset
uspto-grants-2007_01
Patent number
US07160891B2

Reaction notes

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