Thioglycolic Acid → HCID 57906493, compound

HRID 420543Notes

Reaction equation

HRID 420543 reaction equation
[C:1]([O:5][C:6](=[O:44])[NH:7][CH2:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])=[CH:13][N:12]2[C:23]([N:26]3[CH2:31][CH2:30][N:29](S(C4C=CC=CC=4[N+]([O-])=O)(=O)=O)[CH2:28][CH2:27]3)=[CH:24][N:25]=[C:11]2[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].O[Li].O.SCC(O)=O.C([O-])(O)=O.[Na+]>CN(C=O)C>[C:1]([O:5][C:6](=[O:44])[NH:7][CH2:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])=[CH:13][N:12]2[C:23]([N:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)=[CH:24][N:25]=[C:11]2[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 1133Thioglycolic AcidHCID 168937Lithium hydroxide, monohydrateHCID 516892Sodium BicarbonateHCID 57906592HCID 57906592, compound

Product 1

HCID 57906493HCID 57906493, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of {6-(2,4-dichloro-phenyl)-3-[4-(2-nitro-benzenesulfonyl)-piperazin-1-yl]-imidazo[1,2-a]pyridin-7-ylmethyl}-carbamic acid tert-butyl ester (2.9 g, 4.38 mmol, prepared following the procedure described for Example 6, Step 3.3 using the adequate cyclisation reagent), LiOH.H2O (1.11 g, 26.3 mmol) and mercaptoacetic acid (0.94 mL, 13.2 mmol) in DMF (20 mL) was stirred at RT for 30 min then poured into a saturated aqueous NaHCO3 solution (200 mL) and extracted with AcOEt (4×200 mL). The combined organic fractions were washed with brine (100 mL), dried over Na2SO4, filtered and evaporated to dryness. The remaining residue was purified by Combi-Flash CompanionT™ (Isco Inc.) column chromatography (SiO2; gradient elution, DCM/[DCM/MeOH—NH3 9:1]95:5→100% [DCM/MeOH—NH3 9:1]) to yield the title compound (1.61 g, 3.38 mmol, 77%) as a yellow foam. MS: 477 [M+1]+; HPLC: AtRet=1.45; TLC: RF 0.33 (DCM/MeOH—NH3 9:1).

Workup

  1. customprepared
  2. extractionextracted with AcOEt (4×200 mL)
  3. washThe combined organic fractions were washed with brine (100 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe remaining residue was purified by Combi-Flash CompanionT™ (Isco Inc.) column chromatography (SiO2
  8. washgradient elution, DCM/[DCM/MeOH—NH3 9:1]95:5→100% [DCM/MeOH—NH3 9:1])

Sources & evidence

ORD record
ord-d34244d57bb74e078534b7b486d21d8c
Source dataset
uspto-grants-2012_01
Patent number
US08097617B2

Reaction notes

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