Hydroxyurea → N-{4-[5-fluoro-3-(4-methoxytetrahydropyran-4-yl)phenylthio]-alpha-methylbenzyloxy}urea

HRID 1741660Notes

Reaction equation

HRID 1741660 reaction equation
[OH:1][NH:2][C:3]([NH2:5])=[O:4].Cl[CH:7]([C:9]1[CH:14]=[CH:13][C:12]([S:15][C:16]2[CH:17]=[C:18]([C:23]3([O:29][CH3:30])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[CH:19]=[C:20]([F:22])[CH:21]=2)=[CH:11][CH:10]=1)[CH3:8]>>[F:22][C:20]1[CH:19]=[C:18]([C:23]2([O:29][CH3:30])[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)[CH:17]=[C:16]([S:15][C:12]2[CH:11]=[CH:10][C:9]([CH:7]([CH3:8])[O:1][NH:2][C:3]([NH2:5])=[O:4])=[CH:14][CH:13]=2)[CH:21]=1

Participants

3

Reactant 2

HCID 3657HydroxyureaHCID 193799314-{3-[4-(1-Chloroethyl)phenylthio]-5-fluorophenyl}-4-methoxytetrahydropyran

Product 1

HCID 19010619N-{4-[5-fluoro-3-(4-methoxytetrahydropyran-4-yl)phenylthio]-alpha-methylbenzyloxy}ureaYield 32%

Conditions

Temperature
60 °C

Procedure

Using an analogous procedure to that described in Example 1 except that the reactants were heated to 60° C. for 2 hours, hydroxyurea was reacted with 4-{3-[4-(1-chloroethyl)phenylthio]-5-fluorophenyl}-4-methoxytetrahydropyran to give N-{4-[5-fluoro-3-(4-methoxytetrahydropyran-4-yl)phenylthio]-α-methylbenzyloxy}urea in 32% yield, m.p. 84°-85° C.

Sources & evidence

ORD record
ord-3ec7fa72e62f4c71a83c6466766f01f1
Source dataset
uspto-grants-1994_08
Patent number
US05334614

Reaction notes

Loading…