Diisopropylethylamine → N-(4-(6-Cyano-7-(2-methoxyethoxy)-4-quinolyl)oxyphenyl)-N'-(3-(methylsulfonyl)phenyl)urea

HRID 1433355Notes

Reaction equation

HRID 1433355 reaction equation
C(N(C(C)C)CC)(C)C.[CH3:10][S:11]([C:14]1[CH:15]=[C:16]([NH:20][C:21](=[O:29])OC2C=CC=CC=2)[CH:17]=[CH:18][CH:19]=1)(=[O:13])=[O:12].[NH2:30][C:31]1[CH:54]=[CH:53][C:34]([O:35][C:36]2[C:45]3[C:40](=[CH:41][C:42]([O:48][CH2:49][CH2:50][O:51][CH3:52])=[C:43]([C:46]#[N:47])[CH:44]=3)[N:39]=[CH:38][CH:37]=2)=[CH:33][CH:32]=1>>[C:46]([C:43]1[CH:44]=[C:45]2[C:40](=[CH:41][C:42]=1[O:48][CH2:49][CH2:50][O:51][CH3:52])[N:39]=[CH:38][CH:37]=[C:36]2[O:35][C:34]1[CH:33]=[CH:32][C:31]([NH:30][C:21]([NH:20][C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([S:11]([CH3:10])(=[O:12])=[O:13])[CH:15]=2)=[O:29])=[CH:54][CH:53]=1)#[N:47]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 22936234Phenyl 3-methylsulfonylphenylcarbamateHCID 229365064-(4-Aminophenoxy)-6-cyano-7-(2-methoxyethoxy)quinoline

Product 1

HCID 10208780N-(4-(6-Cyano-7-(2-methoxyethoxy)-4-quinolyl)oxyphenyl)-N'-(3-(methylsulfonyl)phenyl)ureaYield 75.6%

Procedure

Diisopropylethylamine (0.057 ml, 0.328 mmol) and phenyl N-[3-(methylsulfonyl)phenyl]carbamate (96 mg, 0.328 mmol) were reacted with 4-(4-aminophenoxy)-7-(2-methoxyethoxy)-6-cyanoquinoline (100 mg, 0.298 mmol), and the title compound (120 mg, 0.225 mmol, 75.6%) was obtained as white crystals by the same procedure as in Example 34.

Sources & evidence

ORD record
ord-c9df8169b9c745b083feea2c20bdd897
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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