Triethylamine → 3-{3-[(4-Cyanophenylamino)-(5-fluoro-8-methoxy-2,3-dihydrobenzo[1,4]dioxin-6-yl)methyl]-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}thiophene-2-carboxylic acid methyl ester

HRID 1161522Notes

Reaction equation

HRID 1161522 reaction equation
CO[C:3](=[O:31])[N:4]=[C:5](SC)[C:6](=[N:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=1)[C:7]1[CH:16]=[C:15]([O:17][CH3:18])[C:10]2[O:11][CH2:12][CH2:13][O:14][C:9]=2[C:8]=1[F:19].[CH3:32][O:33][C:34]([C:36]1[S:37][CH:38]=[CH:39][C:40]=1[NH:41][NH2:42])=[O:35].C(N(CC)CC)C>CN(C=O)C>[CH3:32][O:33][C:34]([C:36]1[S:37][CH:38]=[CH:39][C:40]=1[N:41]1[C:3](=[O:31])[NH:4][C:5]([CH:6]([NH:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]#[N:28])=[CH:25][CH:26]=2)[C:7]2[CH:16]=[C:15]([O:17][CH3:18])[C:10]3[O:11][CH2:12][CH2:13][O:14][C:9]=3[C:8]=2[F:19])=[N:42]1)=[O:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2777595Methyl 3-Hydrazinothiophene-2-CarboxylateHCID 72312729[2-(4-Cyanophenylimino)-2-(5-fluoro-8-methoxy-2,3-dihydrobenzo[1,4]dioxin-6-yl)-1-methylsulfanylethylidene]carbamic acid methyl ester

Product 1

HCID 1359821453-{3-[(4-Cyanophenylamino)-(5-fluoro-8-methoxy-2,3-dihydrobenzo[1,4]dioxin-6-yl)methyl]-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}thiophene-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 2 g of [2-(4-cyanophenylimino)-2-(5-fluoro-8-methoxy-2,3-dihydrobenzo[1,4]dioxin-6-yl)-1-methylsulfanylethylidene]carbamic acid methyl ester in 24 ml of DMF there were added 720 mg of 3-hydrazinothiophene-2-carboxylic acid methyl ester and 1.2 ml of triethylamine, and the mixture was stirred overnight at 85° C. under a nitrogen atmosphere.

Sources & evidence

ORD record
ord-2add5429012d490880aaba2b35747f4c
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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