3-(Chloromethyl)pyridine hydrochloride → 4-(3-Chloro-4-fluoroanilino)-7-methoxy-6-(3-pyridylmethoxy)quinazoline

HRID 2184679Notes

Reaction equation

HRID 2184679 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[F:22])[NH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:17][CH3:18])=[C:13]([OH:16])[CH:14]=2)[N:9]=[CH:8][N:7]=1.Cl.Cl[CH2:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[F:22])[NH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:17][CH3:18])=[C:13]([O:16][CH2:25][C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)[CH:14]=2)[N:9]=[CH:8][N:7]=1

Participants

3

Reactant 2

HCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 104712174-[(3-Chloro-4-fluorophenyl)amino]-7-methoxyquinazolin-6-ol

Product 1

HCID 224784054-(3-Chloro-4-fluoroanilino)-7-methoxy-6-(3-pyridylmethoxy)quinazolineYield 18%

Procedure

Using an analogous procedure to that described in Example 32, 4-(3-chloro-4-fluoroanilino)-6-hydroxy-7-methoxyquinazoline was reacted with 3-chloromethylpyridine, hydrochloride salt to give 4-(3-chloro-4-fluoroanilino)-7-methoxy-6-(3-pyridylmethoxy)quinazoline in 18% yield; NMR Spectrum: 3.93 (s, 3H), 5.28 (s, 2H), 7.16 (s, 1H), 7.4 (m, 2H), 7.75 (m, 1H), 7.95 (m, 1H), 8.1 (m, 2H), 8.4 (s, 1H), 8.6 (m, 1H), 8.75 (m, 1H); Elemental Analysis: Found C, 61.0; H, 3.9; N, 13.5; C21H16ClFN4O2 requires C, 61.4; H, 3.9; N, 13.6%.

Sources & evidence

ORD record
ord-8f43979cd9ef48f8ba30dcb8c643bf8a
Source dataset
uspto-grants-2002_06
Patent number
US06399602B1

Reaction notes

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