Hydrochloric Acid → HCID 86613657, compound

HRID 269284Notes

Reaction equation

HRID 269284 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[N:8]2[N:9]=[CH:10][C:11]([C:12]#[C:13][C:14]3[CH:15]=[CH:16][C:17]([NH2:20])=[N:18][CH:19]=3)=[C:7]2[N:6]=[C:5]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[CH:4]=1.[NH4+].[OH-].Cl.O.[C:37](OC(=O)C)(=[O:39])[CH3:38]>C1COCC1>[F:32][C:2]([F:1])([F:31])[C:3]1[N:8]2[N:9]=[CH:10][C:11]([C:12]#[C:13][C:14]3[CH:15]=[CH:16][C:17]([NH:20][C:37](=[O:39])[CH3:38])=[N:18][CH:19]=3)=[C:7]2[N:6]=[C:5]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:23][CH:22]=2)[CH:4]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 7918Acetic AnhydrideHCID 14923Ammonium HydroxideHCID 71533696Decoglurant

Product 1

HCID 86613657HCID 86613657, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-[7-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidin-3-ylethynyl]-pyridin-2-ylamine (example 55) (2.00 g, 4.47 mmol) in acetic anhydride (15 mL) was stirred at 120° C. for 1 h. Cooled to 60° C., concentrated in vaccum to dryness (water bath temperature 60° C.) and dried in HV to give an orange solid (2.465 g, 113%, mixture of mono- and diacetylated compound). Suspended in THF (30 mL) at 23° C., added NH4OH (25%, 13.3M, 1.0 mL, 13.4 mmol) and stirred at 23° C. for 1.5 h resulting in a clear red solution, adjusted pH with 1N HCl until pH 1, added H2O (total volume 200 mL), filtered the precipitate off, washed with H2O and dried in HV, followed by trituration with ether and drying in HV to give the title compound as an orange solid (2.130 g, 97%). MS [ISN] 488.1[(M−H)−]; mp 266° C.

Workup

  1. temperatureCooled to 60° C.
  2. concentrationconcentrated in vaccum to dryness (water bath temperature 60° C.)
  3. customdried in HV
  4. customto give
  5. additionan orange solid (2.465 g, 113%, mixture of mono- and diacetylated compound)
  6. stirringstirred at 23° C. for 1.5 h
  7. customresulting in a clear red solution
  8. filtrationfiltered the precipitate off,
  9. washwashed with H2O
  10. customdried in HV
  11. customdrying in HV

Sources & evidence

ORD record
ord-24754e42e56447dc9ec58fa2545206b9
Source dataset
uspto-grants-2008_11
Patent number
US07446113B2

Reaction notes

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