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

HRID 1010091Notes

Reaction equation

C(N(C(C)C)CC)(C)C.C1(O[C:17](=[O:29])[NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([S:25]([CH3:28])(=[O:27])=[O:26])[CH:20]=2)C=CC=CC=1.[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:17]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([S:25]([CH3:28])(=[O:26])=[O:27])[CH:20]=2)=[O:29])=[CH:54][CH:53]=1)#[N:47]

Participants

Reactant 3

HCID 81531Diisopropylethylamine

HCID 22936234Phenyl 3-methylsulfonylphenylcarbamate

HCID 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 phenylN-[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-6c7ddb57f7414a23b83f6a8fcf147cdc
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07973160B2

Reaction notes

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