Hydrochloric Acid → HCID 67415371, compound

HRID 1175072Notes

Reaction equation

HRID 1175072 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([Cl:20])=[N:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[O:21][CH3:22])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:23][C:24]1[C:25]([F:31])=[C:26]([CH:28]=[CH:29][CH:30]=1)[NH2:27]>O1CCOCC1.C(#N)C>[ClH:20].[CH2:2]([O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([NH:27][C:26]3[CH:28]=[CH:29][CH:30]=[C:24]([Cl:23])[C:25]=3[F:31])=[N:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[O:21][CH3:22])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 750143-Chloro-2-fluoroanilineHCID 106619987-(Benzyloxy)-4-chloro-6-methoxyquinazoline

Product 1

HCID 67415371HCID 67415371, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

4.0M HCl in Dioxane (4.0 ml) was added to a stirred suspension of 7-(benzyloxy)-4-chloro-6-methoxyquinazoline (60 g, 0.2 mol) [prepared as described in WO98/13354, Example 1] and 3-chloro-2-fluoroaniline (31.96 g, 0.22 mol) in acetonitrile (1200 mL). The reaction mixture was heated at 80° C. for 1 hour then left to stand O/N. Acetonitrile (500 mL) was added and the resulting precipitate filtered, washed with Acetonitrile (3×500 mL) and dried under vacuum to give 7-(benzyloxy)-N-(3-chloro-2-fluorophenyl)-6-methoxyquinazolin-4-amine hydrochloride 2 as a beige solid (85.45 g, 96%); 1H NMR Spectrum: (DMSO d6) 4.02 (s, 3H), 5.35 (s, 2H), 7.30-7.60 (m, 9H), 7.65 (m, 1H), 8.38 (s, 1H), 8.85 (s, 1H), 11.8 (s, 1H); Mass Spectrum: (M+H)+ 410.27.

Workup

  1. customprepared
  2. waitthen left
  3. filtrationthe resulting precipitate filtered
  4. washwashed with Acetonitrile (3×500 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-8797baa9e8ea400c86c1edc0b83892b8
Source dataset
uspto-grants-2010_11
Patent number
US07838530B2

Reaction notes

Loading…