Ammonia → HCID 10114823, compound

HRID 495388Notes

Reaction equation

HRID 495388 reaction equation
Cl.Cl.C([O:6][CH:7]([CH2:32][N:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1)[CH2:8][O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([NH:20][C:21]3[C:26]4[CH:27]=[CH:28][O:29][C:25]=4[CH:24]=[CH:23][CH:22]=3)=[N:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[O:30][CH3:31])(=O)C.N.Cl.C(OCC)C>C(Cl)Cl.C(O)(C)C>[O:29]1[C:25]2[CH:24]=[CH:23][CH:22]=[C:21]([NH:20][C:14]3[C:13]4[C:18](=[CH:19][C:10]([O:9][CH2:8][CH:7]([OH:6])[CH2:32][N:33]5[CH2:34][CH2:35][O:36][CH2:37][CH2:38]5)=[C:11]([O:30][CH3:31])[CH:12]=4)[N:17]=[CH:16][N:15]=3)[C:26]=2[CH:27]=[CH:28]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 22326507HCID 22326507, compound

Product 1

HCID 10114823HCID 10114823, compoundYield 115.7%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 7-(2-acetoxy-3-morpholinopropoxy)-4-(4-benzofuranylamino)-6-methoxyquinazoline dihydrochloride (0.14 g) and a saturated methanolic ammonia solution (3 ml) was stirred at ambient temperature overnight. The solvent was removed by evaporation and the mixture was dissolved in methylene chloride (3 ml) and adsorbed on the top of a pre-packed chromatography column containing 5 g of NH2-silica (Isolute sorbent from International Sorbent Technology Ltd, ref 9470-0100) and eluted with a 19:1 mixture of methylene chloride and methanol. The material so obtained was dissolved in methylene chloride (3 ml) and a 6M solution of hydrogen chloride in isopropanol (0.3 ml) was added with stirring. Diethyl ether (10 ml) was added and the resultant precipitate was collected, rinsed with diethyl ether and dried under vacuum. There was thus obtained the title compound (0.129 g); NMR Spectrum: (DMSOd6 and CF3CO2D) 3.15-3.48 (m, 4H), 4.56 (d, 2H), 3.76-3.94 (m, 2H), 3.94-4.06 (m, 2H), 4.06 (s, 3H), 4.26 (d, 2H), 4.53-4.61 (m, 1H), 6.91 (d, 1H), 7.4 (d, 1H), 7.46 (m, 1H), 7.51 (s, 1H), 7.55 (s, 1H), 8.03 (d, 1H), 8.38 (s, 1H), 8.8 (s, 1H); Mass Spectrum: M+H+ 451.

Workup

  1. customThe solvent was removed by evaporation
  2. dissolutionthe mixture was dissolved in methylene chloride (3 ml)
  3. additioncontaining 5 g of NH2-silica (Isolute sorbent from International Sorbent Technology Ltd, ref 9470-0100)
  4. washeluted with a 19:1 mixture of methylene chloride and methanol
  5. customThe material so obtained
  6. customthe resultant precipitate was collected
  7. washrinsed with diethyl ether
  8. customdried under vacuum

Sources & evidence

ORD record
ord-3cb560df12be46ed9358ddd8d4665294
Source dataset
uspto-grants-2005_09
Patent number
US06939866B2

Reaction notes

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