Ammonia → HCID 21935987, compound

HRID 1371489Notes

Reaction equation

HRID 1371489 reaction equation
[ClH:1].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[CH:26]=[CH:25][CH:24]=[C:23]4[O:27][CH2:28][O:29][C:22]=34)=[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>[ClH:1].[ClH:1].[OH: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[CH:26]=[CH:25][CH:24]=[C:23]4[O:27][CH2:28][O:29][C:22]=34)=[N:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[O:30][CH3:31]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 21936025HCID 21936025, compound

Product 1

HCID 21935987HCID 21935987, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 7-(2-acetoxy-3-morpholinopropoxy)-6-methoxy-4-(2,3-methylenedioxyanilino)quinazoline dihydrochloride (0.104 g) and a saturated methanolic ammonia solution (3 ml) was stirred at ambient temperature for 16 hours. The mixture was evaporated and the residue was purified by column chromatography on silica (Isolute ammonia-treated silica from International Sorbent Technology Limited, catalogue reference 9470-0100) using a 19:1 mixture of methylene chloride and methanol as eluent. 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 isolated, washed with diethyl ether and dried under vacuum. There was thus obtained the title compound (0.095 g); NMR Spectrum: (DMSOd6 and CF3CO2D) 3.15–3.45 (m, 4H), 3.54 (d, 2H), 3.743.91 (d, 2H), 3.97 (d, 2H), 4.02 (s, 3H), 4.24 (d, 2H), 4.49–4.58 (m, 1H), 6.08 (s, 2H), 6.96–7.04 (m, 3H), 7.47 (s, 1H), 8.23 (s, 1H), 8.88 (s, 1H); Mass Spectrum: M+H+ 455.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was purified by column chromatography on silica (Isolute ammonia-treated silica from International Sorbent Technology Limited, catalogue reference 9470-0100)
  3. additiona 19:1 mixture of methylene chloride and methanol as eluent
  4. customThe material so obtained

Sources & evidence

ORD record
ord-3903377b33194ddebefdcc57b2e18fe8
Source dataset
uspto-grants-2007_01
Patent number
US07157467B2

Reaction notes

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