Triethylamine → N-({4-bromo-6-[(methylcarbamoyl)amino]pyridin-2-yl}carbamoyl)-5-methylthiophene-3-sulfonamide

HRID 1696729Notes

Reaction equation

[CH3:1][C:2]1[S:6][CH:5]=[C:4]([S:7]([NH2:10])(=[O:9])=[O:8])[CH:3]=1.[C:11]1([O:17]C(Cl)=O)C=CC=CC=1.C(N(CC)CC)C.[NH2:28][C:29]1[N:34]=[C:33]([NH:35][C:36]([NH:38][CH3:39])=[O:37])[CH:32]=[C:31]([Br:40])[CH:30]=1>C(#N)C>[Br:40][C:31]1[CH:32]=[C:33]([NH:35][C:36](=[O:37])[NH:38][CH3:39])[N:34]=[C:29]([NH:28][C:11]([NH:10][S:7]([C:4]2[CH:3]=[C:2]([CH3:1])[S:6][CH:5]=2)(=[O:9])=[O:8])=[O:17])[CH:30]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 0.089 g 5-methyl-thiophene-3-sulfonic acid amide (example 2a) in 4 ml acetonitrile was added at 0° C. 0.094 g phenylchloroformate and 0.127 g triethylamine. The mixture was stirred at 0° C. for 1 h. To the resulting suspension was added 0.127 g 1-(6-amino-4-bromo-pyridin-2-yl)-3-methyl-urea and the mixture was heated to 60° C. for 18 h. The reaction mixture was partitioned between water and ethyl acetate. The phases were separated and the pH of the aqueous phase was adjusted to 2 by addition of 1N hydrochloric acid. The product was extracted with ethyl acetate. The organic phase was washed with water and brine, dried over sodium sulfate and evaporated to yield 0.080 g of the title compound as an orange yellow powder. MS (ISN) M−H+=445.8 and 447.7

Workup

temperaturethe mixture was heated to 60° C. for 18 h
customThe reaction mixture was partitioned between water and ethyl acetate
customThe phases were separated
additionthe pH of the aqueous phase was adjusted to 2 by addition of 1N hydrochloric acid
extractionThe product was extracted with ethyl acetate
washThe organic phase was washed with water and brine
dry with materialdried over sodium sulfate
customevaporated

Sources & evidence

ORD record: ord-98a83099f6de41859c9b67a827dc0ce4
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163778B2

Reaction notes

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