Acetic Acid → HCID 54711175, compound

HRID 1244110Notes

Reaction equation

HRID 1244110 reaction equation
[Cl:1][C:2]1[S:14][C:5]2[NH:6][C:7](=[O:13])[C:8]([C:11]#[N:12])=[C:9]([OH:10])[C:4]=2[C:3]=1[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]2([OH:28])[CH2:27][CH:26]=[CH:25][CH2:24]2)=[CH:17][CH:16]=1.[N+](C([O-])=O)(C([O-])=O)=[N-].[K+].[K+].CC(O)=O>CS(C)=O.CO>[Cl:1][C:2]1[S:14][C:5]2[NH:6][C:7](=[O:13])[C:8]([C:11]#[N:12])=[C:9]([OH:10])[C:4]=2[C:3]=1[C:15]1[CH:16]=[CH:17][C:18]([O:21][CH2:22][C:23]2([OH:28])[CH2:24][CH2:25][CH2:26][CH2:27]2)=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 21931495HCID 21931495, compoundHCID 54678077HCID 54678077, compound

Product 1

HCID 54711175HCID 54711175, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent2×

Procedure

To an ambient slurry of 2-chloro-4-hydroxy-3-{4-[(1-hydroxycyclopent-3-en-1-yl)methoxy]phenyl}-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile (60 mg, 0.15 mmol) and potassium diazodicarboxylate (88 mg, 0.45 mmol) in a mixture of DMSO (1.0 mL) and MeOH (1.3 mL) was slowly added a solution of AcOH (0.051 mL, 0.90 mmol) in MeOH (0.30 mL). After 10 minutes, the reaction was quenched by the addition of 1N HCl (10 mL) and EtOAc (5 mL). The layers were separated, and the aqueous was extracted with additional EtOAc (2×5 mL). The combined organic layers were dried with anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by RPLC to give the titled compound as a white solid. MS (ESI) m/e 415 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ ppm 1.67 (m, 8H), 3.88 (s, 2H), 6.94 (d, J=8.82 Hz, 2H), 7.22 (d, J=8.82 Hz, 2H).

Workup

  1. customthe reaction was quenched by the addition of 1N HCl (10 mL) and EtOAc (5 mL)
  2. customThe layers were separated
  3. extractionthe aqueous was extracted with additional EtOAc (2×5 mL)
  4. dry with materialThe combined organic layers were dried with anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by RPLC

Sources & evidence

ORD record
ord-d2744bece0484a97a54ec0a79c81c439
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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