Hydrochloric Acid → HCID 178434552, compound

HRID 1094788Notes

Reaction equation

HRID 1094788 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]([C:11]2[C:12]([CH3:24])=[N:13][N:14](COCC[Si](C)(C)C)[CH:15]=2)=[O:10])[CH:5]=[CH:4][C:3]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[O:31][C:32]([F:35])([F:34])[F:33].NC1N=C(NC(C2C(C)N(COCC[Si](C)(C)C)NC=2)=O)C=CC=1C1C=CC=CC=1OC(F)(F)F.Cl>CO.O.O1CCOCC1>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]([C:11]2[C:12]([CH3:24])=[N:13][NH:14][CH:15]=2)=[O:10])[CH:5]=[CH:4][C:3]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[O:31][C:32]([F:33])([F:35])[F:34]

Participants

7

Reactant 3

HCID 313Hydrochloric Acid2×HCID 57582317HCID 57582317, compoundHCID 66637027HCID 66637027, compound

Product 1

HCID 178434552HCID 178434552, compoundYield 32%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A mixture of N-{6-amino-5-[2-(trifluoromethoxy)phenyl]pyridin-2-yl}-3-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazole-4-carboxamide and N-{6-amino-5-[2-(trifluoromethoxy)phenyl]pyridin-2-yl}-3-methyl-2-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazole-4-carboxamide (Preparation 18 as a mixture of regioisomers, 0.050 g, 0.1 mmol) was stirred in methanol (1 ml) and water (0.5 ml). To this was added HCl in 1,4-dioxane (1 ml). The reaction was stirred at room temperature for 18 hours. A further 1 ml of HCl in 1,4-dioxane was added and the reaction stirred for a further 72 hours at room temperature before concentrating in vacuo. The residue was partitioned between ethyl acetate and water. The organic extract was dried over MgSO4 and concentrated in vacuo to yield a gum. The gum was purified by trituration with diethyl ether to afford the title compound as a white solid (0.012 g, 32% yield).

Workup

  1. customPreparation 18
  2. additionas a mixture of regioisomers, 0.050 g, 0.1 mmol)
  3. stirringthe reaction stirred for a further 72 hours at room temperature
  4. concentrationbefore concentrating in vacuo
  5. customThe residue was partitioned between ethyl acetate and water
  6. extractionThe organic extract
  7. dry with materialwas dried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customto yield a gum
  10. customThe gum was purified by trituration with diethyl ether

Sources & evidence

ORD record
ord-04b75940da9f4165b8edd56371db03bc
Source dataset
uspto-grants-2012_03
Patent number
US08134007B2

Reaction notes

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