8-Methoxy-2,3,4,5,6,7-hexahydroazocine → HCID 10380007, compound

HRID 1581694Notes

Reaction equation

HRID 1581694 reaction equation
CO[C:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]=1.[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1([C:22]([NH:24][NH2:25])=O)[CH2:21][CH2:20][CH2:19]1>>[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1([C:22]2[N:10]3[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]3=[N:25][N:24]=2)[CH2:19][CH2:20][CH2:21]1

Participants

3

Reactant 2

HCID 122610598-Methoxy-2,3,4,5,6,7-hexahydroazocineHCID 22722151HCID 22722151, compound

Product 1

HCID 10380007HCID 10380007, compound

Conditions

Temperature
120 °C

Procedure

8-Methoxy-2,3,4,5,6,7-hexahydroazocine (47 μl, 0.412 mmol) was added to the solution of 1-(2-fluorophenyl)cyclobutanecarbohydrazide, and the reaction was stirred at 120° C. overnight. After cooling, the solution was concentrated, and the product was purified by preparative HPLC as the trifluoroacetate salt. The salt was added to a saturated sodium bicarbonate solution and extracted with ethyl acetate to give the freebase. The extract was dried over magnesium sulfate, filtered and evaporated to give the purified triazole (2-34) as a solid (12.5 mg).

Workup

  1. temperatureAfter cooling
  2. concentrationthe solution was concentrated
  3. customthe product was purified by preparative HPLC as the trifluoroacetate salt
  4. additionThe salt was added to a saturated sodium bicarbonate solution
  5. extractionextracted with ethyl acetate
  6. customto give the freebase
  7. dry with materialThe extract was dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-7f497c5e965a4292a88eaa8b3db4dab1
Source dataset
uspto-grants-2004_05
Patent number
US06730690B2

Reaction notes

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