3-(N-methyl-N-(4-pyridyl)amino)propanol → 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-(3-(N-methyl-N-(4-pyridyl)amino)propoxy)quinazoline hydrochloride

HRID 1384594Notes

Reaction equation

HRID 1384594 reaction equation
[CH3:1][N:2]([CH2:9][CH2:10][CH2:11][OH:12])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[Cl:13][C:14]1[CH:33]=[CH:32][C:17]([NH:18][C:19]2[C:28]3[C:23](=[CH:24][C:25](O)=[C:26]([O:29][CH3:30])[CH:27]=3)[N:22]=[CH:21][N:20]=2)=[C:16]([F:34])[CH:15]=1>>[ClH:13].[Cl:13][C:14]1[CH:33]=[CH:32][C:17]([NH:18][C:19]2[C:28]3[C:23](=[CH:24][C:25]([O:12][CH2:11][CH2:10][CH2:9][N:2]([CH3:1])[C:3]4[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=4)=[C:26]([O:29][CH3:30])[CH:27]=3)[N:22]=[CH:21][N:20]=2)=[C:16]([F:34])[CH:15]=1

Participants

3

Reactant 2

HCID 226250383-(N-methyl-N-(4-pyridyl)amino)propanolHCID 1355137204-(4-Chloro-2-fluorophenylamino)-7-hydroxy-6-methoxyquinazoline

Product 1

HCID 226249124-(4-chloro-2-fluoroanilino)-6-methoxy-7-(3-(N-methyl-N-(4-pyridyl)amino)propoxy)quinazoline hydrochlorideYield 119%

Procedure

Using a procedure analogous to that described in Example 47, 3-(N-methyl-N-(4-pyridyl)amino)propanol (116 mg, 0.7mmol) was treated with 4-(4-chloro-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline (160 mg, 0.5 mmol), (prepared as described for the starting material in Example 24), to give 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-(3-(N-methyl-N-(4-pyridyl)amino)propoxy)quinazoline hydrochloride (150 mg, 55%). m.p. 243-248° C. 1H NMR Spectrum: (DMSOd6; CD3COOD) 2.2(t, 2H); 3.21(t, 3H); 3.82(t, 2H); 4.0(s, 3H); 4.31(t, 2H); 6.95(br s, 1H); 7.2(br s, 1H); 7.39(s, 1H); 7.46(dd, 1H); 7.62(t, 1H); 7.68(dd, 1H); 8.2(s, 1H); 8.3(br s, 2H); 8.87(s, 1H) MS-ESI: 468 [MH]+

Workup

  1. custom(prepared

Sources & evidence

ORD record
ord-8f6d0da6668442acbf559d84f2200792
Source dataset
uspto-grants-2001_07
Patent number
US06258951B1

Reaction notes

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