Ammonia → HCID 22591484, compound

HRID 22780Notes

Reaction equation

HRID 22780 reaction equation
[ClH:1].Cl.C([O:6][CH:7]([CH2:33][N:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1)[CH2:8][O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([NH:20][C:21]3[C:29]4[O:28][CH:27]=[C:26]([Cl:30])[C:25]=4[CH:24]=[CH:23][CH:22]=3)=[N:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[O:31][CH3:32])(=O)C.N.Cl.C(OCC)C>C(Cl)Cl.C(O)(C)C>[ClH:30].[ClH:1].[Cl:30][C:26]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])[CH2:33][N:34]5[CH2:35][CH2:36][O:37][CH2:38][CH2:39]5)=[C:11]([O:31][CH3:32])[CH:12]=4)[N:17]=[CH:16][N:15]=3)[C:29]=2[O:28][CH:27]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 225914637-(2-Acetoxy-3-morpholinopropoxy)-4-(3-chlorobenzofuran-7-ylamino)-6-methoxyquinazoline dihydrochloride

Product 1

HCID 22591484HCID 22591484, compoundYield 157.7%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 7-(2-acetoxy-3-morpholinopropoxy)-4-(3-chlorobenzofuran-7-ylamino)-6-methoxyquinazoline dihydrochloride (0.15 g) and a saturated methanolic ammonia solution (3 ml) was stirred at ambient temperature overnight. The solvent was evaporated and the residue was dissolved in methylene chloride (3 ml) and adsorbed to the top of a pre-packed silica column (NH2-silica; Isolute sorbent from International Sorbent Technology Ltd, ref. no. 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. Diethyl ether (10 ml) was added and the resultant precipitate was collected by filtration, washed with diethyl ether and dried under vacuum. There was thus obtained the title compound (0.11 g); Mass Spectrum: M+H+ 486.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in methylene chloride (3 ml)
  3. wash9470-0100) and eluted with a 19:1 mixture of methylene chloride and methanol
  4. customThe material so obtained
  5. filtrationthe resultant precipitate was collected by filtration
  6. washwashed with diethyl ether
  7. customdried under vacuum

Sources & evidence

ORD record
ord-cbcf7b8e2c574d008b20c6dbf4655f6e
Source dataset
uspto-grants-2005_02
Patent number
US06849625B2

Reaction notes

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