Water → N-(4-(6-Cyano-7-(2-methoxyethoxy)-4-quinolyl)oxyphenyl)-N'-(2-pyridyl)urea

HRID 387703Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][O:16][CH3:17])[N:9]=[CH:8][CH:7]=[C:6]2[O:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26](=O)[O:27]C2C=CC=CC=2)=[CH:21][CH:20]=1)#[N:2].[NH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=1.C(OCC)(=O)C.O>CS(C)=O>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][O:16][CH3:17])[N:9]=[CH:8][CH:7]=[C:6]2[O:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([NH:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=2)=[O:27])=[CH:21][CH:20]=1)#[N:2]

Participants

Conditions

Temperature: 85 °C

Procedure

Phenyl N-(4-(6-cyano-7-(2-methoxyethoxy)-4-quinolyl)oxyphenyl)carbamate (104 mg, 0.228 mmol) was dissolved in dimethylsulfoxide (1 ml), and then 2-aminopyridine (43 mg, 0.457 mmol) was added and the mixture was heated at 85° C. for 3 hours while stirring. After cooling, ethyl acetate and water were added for distribution, and the organic layer was washed with saturated saline and dried over anhydrous sodium sulfate. After filtering off the drying agent and concentrating under reduced pressure, ethyl acetate-hexane was added to the residue and the precipitated crystals were filtered out and dried under reduced pressure to obtain the title compound (86 mg, 0.189 mmol, 82.7%) as white crystals.

Workup

temperatureAfter cooling
washthe organic layer was washed with saturated saline
dry with materialdried over anhydrous sodium sulfate
filtrationAfter filtering off the drying agent
concentrationconcentrating under reduced pressure, ethyl acetate-hexane
additionwas added to the residue
filtrationthe precipitated crystals were filtered out
customdried under reduced pressure

Sources & evidence

ORD record: ord-6be824cf7cc14d49a36fd3afdccc39f3
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372981B2

Reaction notes

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