(3-Methyloxetan-3-yl)methyl 4-methylbenzenesulfonate → HCID 19077524, compound

HRID 964568Notes

Reaction equation

HRID 964568 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.[CH3:23][C:24]1([CH2:28]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:27][O:26][CH2:25]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][CH2:23][C:24]3([CH3:28])[CH2:27][O:26][CH2:25]3)[CH:14]=2)[N:9]=[CH:8][N:7]=1

Participants

3

Reactant 2

HCID 5461213(3-Methyloxetan-3-yl)methyl 4-methylbenzenesulfonateHCID 104712174-[(3-Chloro-4-fluorophenyl)amino]-7-methoxyquinazolin-6-ol

Product 1

HCID 19077524HCID 19077524, compoundYield 24%

Procedure

Using an analogous procedure to that described in Example 5 except that the reaction mixture was stirred at ambient temperature for 72 hours, 4-(3'-chloro-4'-fluoroanilino)-6-hydroxy-7-methoxyquinazoline was reacted with 3-methyl-3-(4-toluenesulphonyloxymethyl)-oxetane (Chem. Pharm. Bull., 1985, 33, 1707) to give 4-(3'-chloro-4'-fluoroanilino)-7-methoxy-6-(3-methyloxetan-3-ylmethoxy)quinazoline in 24% yield, m.p. 226°-227° C. (recrystallised from ethanol); NMR Spectrum: 1.43 (s, 3H), 3.93 (s, 3H), 4.23 (s, 2H), 4.37 (d, 2H), 4.53 (d, 2H), 7.2 (s, 1H), 7.43 (t, 1H), 7.78 (m, 1H), 7.88 (s, 1H), 8.11 (m, 1H), 8.49 (s, 1H), 9.49 (s, 1H); Elemental Analysis: Found C, 59.5; H, 4.7; N, 10.2; C20H19ClFN3O3 requires C, 59.5; H, 4.7; N, 10.4%.

Sources & evidence

ORD record
ord-2847d02a33434294ac691e7f46e01fb9
Source dataset
uspto-grants-1998_06
Patent number
US05770603

Reaction notes

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