Hydrochloric Acid → HCID 22252938, compound

HRID 1612064Notes

Reaction equation

HRID 1612064 reaction equation
[S:1]1[C:5]2=[N:6][C:7]3[NH:8][C:9]4[C:14]([C:15]=3[C:16]([C:17]([O:19]C)=[O:18])=[C:4]2[CH:3]=[CH:2]1)=[CH:13][CH:12]=[CH:11][CH:10]=4.Cl>>[CH2:15]([N:8]1[C:7]2[N:6]=[C:5]3[S:1][CH:2]=[CH:3][C:4]3=[C:16]([C:17]([OH:19])=[O:18])[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:14]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 85628847HCID 85628847, compound

Product 1

HCID 22252938HCID 22252938, compoundYield 74%

Procedure

A solution of 9H-1-thia-9,10-diaza-cyclopenta[b]fluorene-4-carboxylic acid, methyl ester, (0.025 g, 0.089 mM) in 3 mL DMF was added to a 60% NaH mineral oil dispersion (0.007 g, 0.178 mM) at room temperature. Following cessation of gas evolution, benzyl bromide (0.012 mL, 0.017 g, 0.098 mM) was added and the mixture stirred at room temperature for 3.5 h. The mixture was diluted with ethyl acetate and H2O, the solvent layers separated, and the aqueous layer extracted with ethyl acetate (4×25 mL). The combined ethyl acetate extracts were washed with H2O, 1N HCl, saturated aqueous NaHCO3 solution, and saturated brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 0.013 g of an oily solid that was identified as unreacted 9H-1-thia-9,10-diaza-cyclopenta[b]fluorene-4-carboxylic acid, methyl ester. Adjusted the above aqueous layer from the initial reaction workup to pH 1 with 1N HCl, and extracted with ethyl acetate (4×25 mL). The combined ethyl acetate extracts were washed with H2O, 1N HCl, and saturated brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 0.023 g (74%) of the title compound 9-benzyl-9H-1-thia-9,10-diaza-cyclopenta[b]fluorene-4-carboxylic acid as a yellow solid (MW 358.42, C21H14N2O2S).

Workup

  1. extractionextracted with ethyl acetate (4×25 mL)
  2. washThe combined ethyl acetate extracts were washed with H2O, 1N HCl, and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-967de8b5f77c470da8b853d4f289f8a9
Source dataset
uspto-grants-2006_01
Patent number
US06992100B2

Reaction notes

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