HCID 86652445, compound → HCID 178474450, compound

HRID 1360887Notes

Reaction equation

HRID 1360887 reaction equation
Br[C:2]1[S:3][C:4]([S:17](=[O:27])(=[O:26])[NH:18][CH:19]2[CH2:24][CH2:23][CH:22]([OH:25])[CH2:21][CH2:20]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>>[OH:25][C@@H:22]1[CH2:23][CH2:24][C@H:19]([NH:18][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:26])=[O:27])[CH2:20][CH2:21]1

Participants

3

Reactant 2

HCID 86652445HCID 86652445, compoundHCID 178418339Butyllithium

Product 1

HCID 178474450HCID 178474450, compound

Conditions

Temperature
-70 °C

Procedure

N-{5-[2-Bromo-5-(4-hydroxy-cyclohexylsulfamoyl)-thiophen-3-yl]-4-methyl-thiazo-2-yl}-acetamide obtained in Step I as described above (120 mg; 0.24 mmol; 1 eq), is dissolved anhydrous TBF (10 ml). The reaction mixture is cooled down to −70° C. and put under nitrogen. n-Butyllithium (1.5 ml; 1.6 M; 2.43 mmol; 8 eq) is added dropwise. The reaction is stirred overnight and quenched with water. Solvents are evaporated and the resulting crude product is purified by preparative HPLC, affording Compound (33) as white-off powder (28 mg; 21%).

Workup

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

Sources & evidence

ORD record
ord-d04e14923b38486fa7aec5a2204d2447
Source dataset
uspto-grants-2011_02
Patent number
US07879888B2

Reaction notes

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