Acetic Acid → HCID 68324081, compound

HRID 573699Notes

Reaction equation

HRID 573699 reaction equation
[Cl:1][C:2]1([S:18]([NH:21][C:22]2[CH:27]=[C:26]([CH3:28])[N:25]=[C:24]3[S:29][C:30]([CH3:40])=[C:31]([C:32]4[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[CH:33]=4)[C:23]=23)(=[O:20])=[O:19])[CH2:7][CH2:6][N:5](C(OCC2C=CC=CC=2)=O)[CH2:4][CH2:3]1.CO.C(O)(=O)C.[H][H]>CCO.[Pd]>[Cl:1][C:2]1([S:18]([NH:21][C:22]2[CH:27]=[C:26]([CH3:28])[N:25]=[C:24]3[S:29][C:30]([CH3:40])=[C:31]([C:32]4[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[CH:33]=4)[C:23]=23)(=[O:20])=[O:19])[CH2:3][CH2:4][NH:5][CH2:6][CH2:7]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 68323812HCID 68323812, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68324081HCID 68324081, compoundYield 11.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Phenylmethyl 4-chloro-4-[({2,6-dimethyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}amino)sulfonyl]-1-piperidinecarboxylate (Example 10) (80 mg, 0.133 mmol) was taken-up in EtOH (5 mL), MeOH (5 mL) and acetic acid (1 mL). 10% Palladium on carbon (14.19 mg, 0.013 mmol) was then added and the reaction mixture was stirred at RT under 2 Bar of hydrogen for 48 h. The reaction mixture was then filtered through celite and the celite was washed with 50 mL of MeOH. The solvent was concentrated to give a residue which was purified by normal phase chromatography, eluting with a gradient from 0-10% 2N NH3 in MeOH in DCM and then further purified by MDAP (basic conditions), to afford the title compound (7 mg). LCMS (A) m/z: 466 [M+1]+, Rt 0.81 min (basic).

Workup

  1. filtrationThe reaction mixture was then filtered through celite
  2. washthe celite was washed with 50 mL of MeOH
  3. concentrationThe solvent was concentrated
  4. customto give a residue which
  5. customwas purified by normal phase chromatography
  6. washeluting with a gradient from 0-10% 2N NH3 in MeOH in DCM
  7. customfurther purified by MDAP (basic conditions)

Sources & evidence

ORD record
ord-7737ba9172ef4d599b806c893796f840
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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