1-(5-amino-4-chloro-2-fluorophenyl)-1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazol-5-one → HCID 178518975, compound

HRID 1608037Notes

Reaction equation

HRID 1608037 reaction equation
NC1C(Cl)=CC(F)=C([N:8]2[C:12](=[O:13])[N:11]([CH2:14][CH2:15][CH2:16][F:17])[N:10]=[N:9]2)C=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[F:17][CH2:16][CH2:15][CH2:14][N:11]1[C:12](=[O:13])[N:8]=[N:9][NH:10]1

Participants

4

Reactant 1

HCID 145516171-(5-amino-4-chloro-2-fluorophenyl)-1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazol-5-one

Product 1

HCID 178518975HCID 178518975, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1.0 g (0.0034 mole) of 1-(5-amino-4-chloro-2-fluorophenyl)-1,4-dihydro-4-(3- fluoropropyl)-5H-tetrazol-5-one in 30 ml of methylene chloride was added 0.20 g (0.0017 mole) of 4-(N,N-dimethyl)aminopyridine, 0.50 g (0.0017 mole) of trifluoromethylsulfonyl anhydride, and an additional 0.20 g (0.0017 mole) of 4-(N,N-dimethyl)aminopyridine. This mixture was stirred at room temperature for 0.5 hour. The resultant solution was extracted with 100 ml of a dilute, aqueous, sodium hydroxide solution. The extract was washed with 50 ml of methylene chloride and was neutralized with concentrated hydrochloric acid. This aqueous solution was extracted several times with ethyl acetate and the extracts were combined. The combined extract was dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated under reduced pressure to leave a thick oil. This oil was purified by column chromatography on silica gel, eluted with methylene chloride'acetone (95:5) to yield 1.0 g of 1-[4-chloro- 2-fluoro-5-(N-trifluoromethylsulfonylamino)phenyl]-1,4-dihydro-4-(3-fluoropropyl-5H-tetrazol-5-one as a solid, m.p. 111°-113° C.

Workup

  1. extractionThe resultant solution was extracted with 100 ml of a dilute
  2. washThe extract was washed with 50 ml of methylene chloride
  3. extractionThis aqueous solution was extracted several times with ethyl acetate
  4. extractionThe combined extract
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated under reduced pressure
  8. customto leave a thick oil
  9. customThis oil was purified by column chromatography on silica gel
  10. washeluted with methylene chloride'acetone (95:5)

Sources & evidence

ORD record
ord-0994b5b3c0b2408c851f0e3ef1a90601
Source dataset
uspto-grants-1989_09
Patent number
US04868321

Reaction notes

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