Acetic Acid → HCID 69132047, compound

HRID 750758Notes

Reaction equation

HRID 750758 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([N:13]3[CH2:18][CH2:17][CH:16]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:15][CH2:14]3)=[CH:8]C=2CO)[S:4][C:3]=1[C:27]([NH2:29])=[O:28].[C-:30]#N.[K+].[C:33]([OH:36])(=[O:35])[CH3:34]>CO.O=[Mn]=O>[CH3:30][O:35][C:33]([C:34]1[C:10]2[C:2]([NH2:1])=[C:3]([C:27](=[O:28])[NH2:29])[S:4][C:5]=2[N:6]=[C:7]([N:13]2[CH2:18][CH2:17][CH:16]([O:19][Si:20]([C:23]([CH3:26])([CH3:24])[CH3:25])([CH3:22])[CH3:21])[CH2:15][CH2:14]2)[CH:8]=1)=[O:36]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 9032Potassium CyanideHCID 23401038HCID 23401038, compound

Product 1

HCID 69132047HCID 69132047, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 400 mg of the above amide, 298 mg KCN, 1.59 g MnO2 and 157 microL acetic acid was suspended in 16 mL MeOH and the reaction was capped and stirred 2 days. The reaction mixture was filtered through diatomaceous earth, concentrated, and flash-chromatographed eluting with 5% MeOH/CH2Cl2 to provide 254 mg (60%) 3-amino-6-[4-(tert-butyl-dimethyl-silanyloxy)-piperidin-1-yl]-2-carbamoyl-thieno[2,3-b]pyridine-4-carboxylic acid methyl ester as determined by NMR(DMDO). Further elution with 25% MeOH/CH2Cl2/1% HOAc brought down 151 mg (36%) of the corresponding carboxylic acid as determined by NMR(DMDO).

Workup

  1. customthe reaction was capped
  2. filtrationThe reaction mixture was filtered through diatomaceous earth
  3. concentrationconcentrated
  4. customflash-chromatographed
  5. washeluting with 5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-8d1dfd5c65774c3680db4c1aeaaa569b
Source dataset
uspto-grants-2008_07
Patent number
US07405225B2

Reaction notes

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