Butyllithium → N-(4-methyl-5-{5-[(1H-tetrazol-5-ylamino)sulfonyl]-3-thienyl}-1,3-thiazol-2-yl)acetamide

HRID 1948442Notes

Reaction equation

Br[C:2]1[S:3][C:4]([S:17](=[O:25])(=[O:24])[NH:18][C:19]2[NH:23][N:22]=[N:21][N:20]=2)=[CH:5][C:6]=1[C:7]1[S:11][C:10]([NH:12][C:13](=[O:15])[CH3:14])=[N:9][C:8]=1[CH3:16].C([Li])CCC>C1COCC1>[CH3:16][C:8]1[N:9]=[C:10]([NH:12][C:13](=[O:15])[CH3:14])[S:11][C:7]=1[C:6]1[CH:5]=[C:4]([S:17]([NH:18][C:19]2[NH:23][N:22]=[N:21][N:20]=2)(=[O:24])=[O:25])[S:3][CH:2]=1

Participants

Conditions

Temperature: -70 °C

Procedure

N-{5-[2-Bromo-5-(1H-tetrazol-5-ylsulfamoyl)-thiophen-3-yl]-4-methyl-thiazol-2-yl}-acetamide obtained in Step I as described above (220 mg; 0.37 mmol; 1 eq), is dissolved in anhydrous THF (20 ml). The reaction mixture is cooled down to −70° C. and put under nitrogen. n-Butyllithium (1.9 ml; 1.6 M; 2.99 mmol; 8 eq) is added dropwise. The reaction is stirred 2 hours and is quenched with water. Solvents are evaporated and the resulting crude product is purified by preparative HPLC, affording Compound (41) as a beige solid (8.5 mg; 6%).

Workup

customis quenched with water
customSolvents are evaporated
customthe resulting crude product is purified by preparative HPLC

Sources & evidence

ORD record: ord-5465b9473c214a48b38658aea055bfa6
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399497B2

Reaction notes

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