HCID 86623156, compound → HCID 11998907, compound

HRID 1948443Notes

Reaction equation

HRID 1948443 reaction equation
Br[C:2]1[S:3][C:4]([S:17]([N:20]2[CH2:24][CH:23]=[CH:22][CH2:21]2)(=[O:19])=[O:18])=[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]([N:20]2[CH2:21][CH2:22][CH2:23][CH2:24]2)(=[O:19])=[O:18])[S:3][CH:2]=1

Participants

4

Reactant 2

HCID 86623156HCID 86623156, compoundHCID 178418339Butyllithium

Product 1

HCID 11998907HCID 11998907, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

N-{5-[2-Bromo-5-(2,5-dihydro-pyrrole-1-sulfonyl)-thiophen-3-yl]-4-methyl-thiazol-2-yl}-acetamide obtained in Step I as described above (612 mg; 1.21 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 (15.5 ml; 1.6 M; 9.69 mmol; 8 eq) is added dropwise. The reaction is stirred 2 hours and is quenched with water. The solvents are evaporated and the crude product is purified by preparative HPLC, affording Compound (42) as white-off solid (36 mg; 8%).

Workup

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

Sources & evidence

ORD record
ord-364f4971a28b486c95314e2660df6533
Source dataset
uspto-grants-2013_03
Patent number
US08399497B2

Reaction notes

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