HCID 86623154, compound → HCID 11998905, compound

HRID 1948440Notes

Reaction equation

HRID 1948440 reaction equation
Br[C:2]1[S:3][C:4]([S:17](=[O:25])(=[O:24])[NH:18][CH2:19][CH:20]([OH:23])[CH2:21][OH:22])=[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:23][CH:20]([CH2:21][OH:22])[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:25])=[O:24]

Participants

4

Reactant 2

HCID 86623154HCID 86623154, compoundHCID 178418339Butyllithium

Product 1

HCID 11998905HCID 11998905, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

N-{5-[2-Bromo-5-(2,3-dihydroxy-propylsulfamoyl)-thiophen-3-yl]-4-methyl-thiazol-2-yl}-acetamide obtained in Step I as described above (790 mg; 1.38 mmol; 1 eq), is dissolved in anhydrous THF (50 ml). The reaction mixture is cooled down to −70° C. and put under nitrogen. n-Butyllithium (6.9 ml; 1.6 M; 11.0 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 (40) as a light pink solid (224 mg; 42%).

Workup

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

Sources & evidence

ORD record
ord-e7e06104f4fa41b3a99b96b0bd9f17fa
Source dataset
uspto-grants-2013_03
Patent number
US08399497B2

Reaction notes

Loading…