Triethylamine → 4-(3-{(4-Cyanophenylamino)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)thiazole-5-carboxylic acid methyl ester

HRID 1161545Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[S:9][CH:8]=[N:7][C:6]=1[NH:10][NH2:11])=[O:4].C(N(CC)CC)C.C[O:20][C:21](=O)[N:22]=[C:23](SC)[C:24](=[N:38][C:39]1[CH:44]=[CH:43][C:42]([C:45]#[N:46])=[CH:41][CH:40]=1)[C:25]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[C:27]([O:33][CH2:34][CH2:35][OH:36])[C:26]=1[F:37]>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[S:9][CH:8]=[N:7][C:6]=1[N:10]1[C:21](=[O:20])[NH:22][C:23]([CH:24]([NH:38][C:39]2[CH:40]=[CH:41][C:42]([C:45]#[N:46])=[CH:43][CH:44]=2)[C:25]2[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[C:27]([O:33][CH2:34][CH2:35][OH:36])[C:26]=2[F:37])=[N:11]1)=[O:4]

Participants

Conditions

Temperature: 60 °C

Procedure

After adding 153 mg of 4-hydrazinothiazole-5-carboxylic acid methyl ester (Example (162c)) and 600 μl of triethylamine to a solution of 394 mg of {2-(4-cyanophenylimino)-2-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]-1-methylsulfanylethylidene}carbamic acid methyl ester in 6 ml of THF, the mixture was stirred at 60° C. for 4 hours under a nitrogen atmosphere. The reaction mixture was concentrated, the residue was dissolved in 5 ml of DMF, 600 μl of triethylamine was added and the mixture was stirred overnight at 85° C.

Workup

concentrationThe reaction mixture was concentrated
dissolutionthe residue was dissolved in 5 ml of DMF
addition600 μl of triethylamine was added
stirringthe mixture was stirred overnight at 85° C.

Sources & evidence

ORD record: ord-dd5a217265e9467e94d1f71337c6433b
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816522B2

Reaction notes

Loading…