HCID 86623151, compound → HCID 11998794, compound

HRID 1948431Notes

Reaction equation

HRID 1948431 reaction equation
Br[C:2]1[S:3][C:4]([S:17]([N:20]2[CH2:25][CH2:24][CH:23]([O:26][CH3:27])[CH2:22][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>[CH3:27][O:26][CH:23]1[CH2:22][CH2:21][N:20]([S:17]([C:4]2[S:3][CH:2]=[C:6]([C:7]3[S:11][C:10]([NH:12][C:13](=[O:15])[CH3:14])=[N:9][C:8]=3[CH3:16])[CH:5]=2)(=[O:18])=[O:19])[CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 86623151HCID 86623151, compoundHCID 178418339Butyllithium

Product 1

HCID 11998794HCID 11998794, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

N-{5-[2-Bromo-5-(4-methoxy-piperidine-1-sulfonyl)-thiophen-3yl]-4-methyl-thiazol-2-yl}-acetamide obtained in Step I as described above (250 mg; 0.51 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 (2 ml; 1.6 M; 4.04 mmol; 8 eq) is added dropwise. The reaction is stirred 40 minutes and quenched with water. Solvents are evaporated and the resulting crude product is purified by preparative HPLC, affording Compound (34) as a white-off powder (127 mg; 47%).

Workup

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

Sources & evidence

ORD record
ord-62a8ec6af7e142e392f9da93c9f97bf5
Source dataset
uspto-grants-2013_03
Patent number
US08399497B2

Reaction notes

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