Hydrochloric Acid → HCID 54678998, compound

HRID 1244097Notes

Reaction equation

HRID 1244097 reaction equation
[OH:1][C:2]1[C:3]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20]COC)=[CH:16][CH:15]=3)=[CH:12][S:11][C:4]=2[NH:5][C:6](=[O:10])[C:7]=1[C:8]#[N:9].Cl>C1COCC1>[OH:1][C:2]1[C:3]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)=[CH:12][S:11][C:4]=2[NH:5][C:6](=[O:10])[C:7]=1[C:8]#[N:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54719979HCID 54719979, compound

Product 1

HCID 54678998HCID 54678998, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-hydroxy-3-[4-(methoxymethoxy)phenyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile (0.1 g, 0.305 mmol) in THF (10 mL) was added 1N HCl (20 mL) in a single portion at room temperature and stirred for 16 h at room temperature. The reaction mixture was concentrated and purified by RP-HPLC to afford the title compound. MS (ESI) m/e 282.9 (M−H)+; 1H NMR (500 MHz, DMSO-d6): δ ppm 12.56 (br s, 1H), 9.45 (br s, 1H), 7.22 (d, 2H), 6.89 (s, 1H), 6.74 (d, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-14dfbab586cb47aeaa051e7b6ec5ed32
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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