Hydrochloric Acid → HCID 22625018, compound

HRID 1384608Notes

Reaction equation

HRID 1384608 reaction equation
[Cl:1][C:2]1[C:8]([OH:9])=[CH:7][C:5]([NH2:6])=[C:4]([F:10])[CH:3]=1.Cl[C:12]1[C:21]2[C:16](=[CH:17][C:18]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=3)=[C:19]([O:22][CH3:23])[CH:20]=2)[N:15]=[CH:14][N:13]=1.Cl>C(O)(C)C>[ClH:1].[Cl:1][C:2]1[C:8]([OH:9])=[CH:7][C:5]([NH:6][C:12]2[C:21]3[C:16](=[CH:17][C:18]([O:24][CH2:25][C:26]4[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=4)=[C:19]([O:22][CH3:23])[CH:20]=3)[N:15]=[CH:14][N:13]=2)=[C:4]([F:10])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1586545-Amino-2-chloro-4-fluorophenolHCID 226249154-Chloro-6-methoxy-7-(4-pyridylmethoxy)quinazoline

Product 1

HCID 22625018HCID 22625018, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-chloro-2-fluoro-3-hydroxyaniline (118 mg, 0.7 mmol), (EP 061741 A2), and 4-chloro-6-methoxy-7-((4-pyridyl)methoxy)quinazoline (200 mg, 0.7 mmol), (prepared as described for the starting material in Example 13), in isopropanol (10 ml) and ethereal hydrogen chloride (5 ml) was heated at 80° C. for 2 hours and the mixture was allowed to cool. The precipitated product was collected by filtration, washed with isopropanol and dried to give 4-(4-chloro-2-fluoro-5-hydroxyanilino)-6-methoxy-7-((4-pyridyl)methoxy)quinazoline hydrochloride (110 mg, 31%). 1H NMR Spectrum: (DMSOd6) 3.96(s, 3H); 5.38(s, 2H); 7.14(d, 1H); 7.24(s, 1H); 7.38(d, 1H); 7.48(d, 2H); 7.82(s, 1H); 8.32(s, 1H); 8.58(d, 2H0; 9.48(s, 1H) MS-ESI: 427 [MH]+

Workup

  1. custom(prepared
  2. temperatureto cool
  3. filtrationThe precipitated product was collected by filtration
  4. washwashed with isopropanol
  5. customdried

Sources & evidence

ORD record
ord-b34bbcbb10bb45848b49d2e293c9aae3
Source dataset
uspto-grants-2001_07
Patent number
US06258951B1

Reaction notes

Loading…