Potassium Carbonate → 4-(4-(2-Methoxyphenoxy)-anilino)-3-cyano-6-methoxy-7-glycidyloxy quinoline

HRID 749065Notes

Reaction equation

HRID 749065 reaction equation
[CH3:1][O:2][C:3]1[CH:31]=[CH:30][CH:29]=[CH:28][C:4]=1[O:5][C:6]1[CH:27]=[CH:26][C:9]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([OH:23])=[C:18]([O:21][CH3:22])[CH:19]=3)[N:14]=[CH:13][C:12]=2[C:24]#[N:25])=[CH:8][CH:7]=1.CC1C=CC(S(O[CH2:43][C@H:44]2[O:46][CH2:45]2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:1][O:2][C:3]1[CH:31]=[CH:30][CH:29]=[CH:28][C:4]=1[O:5][C:6]1[CH:27]=[CH:26][C:9]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:23][CH2:43][CH:44]4[O:46][CH2:45]4)=[C:18]([O:21][CH3:22])[CH:19]=3)[N:14]=[CH:13][C:12]=2[C:24]#[N:25])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 153296Oxiranemethanol, 4-methylbenzenesulfonate, (S)-HCID 1358198314-(4-(2-Methoxyphenoxy)-anilino)-3-cyano-6-methoxy-7-hydroxyquinoline

Product 1

HCID 220485194-(4-(2-Methoxyphenoxy)-anilino)-3-cyano-6-methoxy-7-glycidyloxy quinoline

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 4-(4-(2-methoxyphenoxy)-anilino)-3-cyano-6-methoxy-7-hydroxyquinoline (3.6 g, 8.0 mmole), prepared as described in Example 18 step 2, in DMSO (40 ml) was reacted with (2S)-(+)-glycidyl tosylate (2.3 g, 10 mmole) in the presence of potassium carbonate (2.8 g, 20 mmole) at room temperature for 18 hours. 4-(4-(2-methoxyphenoxy)-anilino)-3-cyano-6-methoxy-7-glycidyloxy quinoline was obtained.

Sources & evidence

ORD record
ord-b3b90d258e0b4e4c9831466cf8f5d109
Source dataset
uspto-grants-2008_07
Patent number
US07402583B2

Reaction notes

Loading…