Formic Acid → HCID 21708620, compound

HRID 649797Notes

Reaction equation

HRID 649797 reaction equation
Cl[C:2]1[CH:9]2[CH2:10][N:5]([CH2:6][CH2:7][CH2:8]2)[CH2:4][C:3]=1[C:11]1[C:12]([O:16][CH2:17][CH2:18][CH2:19][CH3:20])=[N:13][S:14][N:15]=1.C([OH:23])C.C(N(CC)CC)C.[CH:31]([OH:33])=[O:32]>[Pd]>[C:17]([OH:16])(=[O:23])[C:31]([OH:33])=[O:32].[CH2:17]([O:16][C:12]1[C:11]([C:3]2[CH2:4][N:5]3[CH2:10][CH:9]([CH:2]=2)[CH2:8][CH2:7][CH2:6]3)=[N:15][S:14][N:13]=1)[CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 702EthanolHCID 8471TriethylamineHCID 9857998HCID 9857998, compound

Product 1

HCID 21708620HCID 21708620, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst3×

Conditions

Temperature
80 °C

Procedure

To a solution of 4-chloro-3-(3-butoxy-1,2,5-thiadiazol-4-yl)-1-azabicyclo-[3.3.1]non-3-ene (0.63 g, 2.0 mmol) in abs. ethanol (20 ml), triethyl amine (3 ml) and formic acid (1 ml) were added. The reaction mixture was heated to 80° C. under nitrogen. At this temperature palladium on carbon (0.5 g, 5%) was added in one portion. After 15 min. another portion of palladium on carbon (0.25 g, 5%) was added. The last addition of palladium on carbon was repeated twice. After cooling, the reaction mixture was filtered and evaporated. The residue was dissolved in water basified with potassium carbonate and extracted with ether (3×75 ml). The ether extracts were dried and evaporated. The crude compound was purified by column chromatography (eluent: CH2Cl2/MeOH (9:1)), yielding 80 mg of free base. The title compound was crystallized with oxalic acid from acetone/ether in 80 mg yield. (Compound 95). M.p. 150-151° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered
  3. customevaporated
  4. dissolutionThe residue was dissolved in water
  5. extractionextracted with ether (3×75 ml)
  6. dry with materialThe ether extracts were dried
  7. customevaporated
  8. customThe crude compound was purified by column chromatography (eluent: CH2Cl2/MeOH (9:1))

Sources & evidence

ORD record
ord-0bfd67a79ef74d9caf8ef21cd5743ec7
Source dataset
uspto-grants-2001_08
Patent number
US06271229B1

Reaction notes

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