Dimethylamine → HCID 59428122, compound

HRID 75988Notes

Reaction equation

HRID 75988 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[C:16]([NH:17][S:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:23][CH:22]=3)(=[O:20])=[O:19])=[CH:15][C:14]([Cl:31])=[CH:13][N:12]=2)[CH:10]=1)=O)C.[OH-].[Na+].[CH3:34][NH:35][CH3:36].C(N(CC)CC)C>C(O)(=O)C.C1COCC1>[CH3:34][N:35]([CH3:36])[C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[C:16]([NH:17][S:18]([C:21]3[CH:22]=[CH:23][C:24]([C:27]([CH3:29])([CH3:28])[CH3:30])=[CH:25][CH:26]=3)(=[O:20])=[O:19])=[CH:15][C:14]([Cl:31])=[CH:13][N:12]=2)[CH:10]=1)=[O:3]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 25134467HCID 25134467, compound

Product 1

HCID 59428122HCID 59428122, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A 25 mL scintillation vial was charged with 1-[3-(4-tert-butyl-benzenesulfonylamino)-5-chloro-pyridin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (synthesized according to general procedure D, 93 mg, 0.2 mmol), NaOH (2 mL, 1.0 M solution in water), and THF (3 mL). The vial was sealed and stirred at 80° C. for 16 hours. The reaction solution was subsequently neutralized to pH=5 with glacial acetic acid. The mixture was extracted with ethyl acetate (2×10 mL) and the combined organics were concentrated in vacuo. The crude product was subsequently dissolved in 2 mL of THF in a 25 mL scintillation vial. To the resultant solution was added with dimethylamine (0.2 mL, 2.0 M in THF), 1-propanephosphonic anhydride solution (184 mg, 50% solution in ethyl acetate), and triethylamine (41 mg, 0.4 mmol). The vial was sealed and stirred at ambient temperature for 1 hour. The volatiles were then evacuated in vacuo and the residue was purified via preparative HPLC to afford 1-[3-(4-tert-butyl-benzenesulfonylamino)-5-chloro-pyridin-2-yl]-1H-pyrazole-4-carboxylic acid dimethylamide as a white powder: MS (ES) M+H expected 462.1, found 462.0.

Workup

  1. customThe vial was sealed
  2. extractionThe mixture was extracted with ethyl acetate (2×10 mL)
  3. concentrationthe combined organics were concentrated in vacuo
  4. dissolutionThe crude product was subsequently dissolved in 2 mL of THF in a 25 mL scintillation vial
  5. customThe vial was sealed
  6. stirringstirred at ambient temperature for 1 hour
  7. customThe volatiles were then evacuated in vacuo
  8. customthe residue was purified via preparative HPLC

Sources & evidence

ORD record
ord-53640dc7e0144cc1b044d81323d8979c
Source dataset
uspto-grants-2014_09
Patent number
US08835468B2

Reaction notes

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