HCID 86652447, compound → HCID 11998798, compound

HRID 1360892Notes

Reaction equation

HRID 1360892 reaction equation
Br[C:2]1[S:3][C:4]([S:17](=[O:23])(=[O:22])[NH:18][CH2:19][CH2:20][OH:21])=[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>[OH:21][CH2:20][CH2:19][NH:18][S:17]([C:4]1[S:3][CH:2]=[C:6]([C:7]2[S:11][C:10]([NH:12][C:13](=[O:15])[CH3:14])=[N:9][C:8]=2[CH3:16])[CH:5]=1)(=[O:23])=[O:22]

Participants

4

Reactant 2

HCID 86652447HCID 86652447, compoundHCID 178418339Butyllithium

Product 1

HCID 11998798HCID 11998798, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

N-{5-[2-Bromo-5-(2-hydroxy-ethylsulfamoyl)-thiophen-3-yl]-4-methyl-thiazol-2-yl}-acetamide obtained in Step I as described above (1760 mg; 4 mmol; 1 eq), is dissolved in anhydrous THF (100 ml). The reaction mixture is then cooled down to −70° C. and put under nitrogen. n-Butyllithium (48 ml; 1.6 M; 95.9 mmol; 24 eq) is added dropwise. The reaction is stirred 2 hours at −70° C. and quenched with water. Solvents are evaporated and the resulting residue is purified by preparative HPLC, affording Compound (38) as a white solid (135 mg; 9%).

Workup

  1. customquenched with water
  2. customSolvents are evaporated
  3. customthe resulting residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-d3d6b6a82db548b28f7e03decf4aa50c
Source dataset
uspto-grants-2011_02
Patent number
US07879888B2

Reaction notes

Loading…