Methylamine → HCID 22316997, compound

HRID 497253Notes

Reaction equation

HRID 497253 reaction equation
[Cl:1][CH2:2][C:3]1[CH:4]=[C:5]([N:13]2[C:17]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[O:25][CH:26]=[CH:27][CH:28]=4)=[CH:20][CH:19]=3)=[CH:16][C:15]([C:29]([F:32])([F:31])[F:30])=[N:14]2)[CH:6]=[CH:7][C:8]=1[S:9]([CH3:12])(=[O:11])=[O:10].[CH3:33][NH2:34].C([O-])([O-])=O.[K+].[K+]>C1COCC1>[ClH:1].[O:25]1[CH:26]=[CH:27][CH:28]=[C:24]1[C:21]1[CH:22]=[CH:23][C:18]([C:17]2[N:13]([C:5]3[CH:6]=[CH:7][C:8]([S:9]([CH3:12])(=[O:10])=[O:11])=[C:3]([CH:4]=3)[CH2:2][NH:34][CH3:33])[N:14]=[C:15]([C:29]([F:31])([F:32])[F:30])[CH:16]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 11430Potassium CarbonateHCID 22316912HCID 22316912, compound

Product 1

HCID 22316997HCID 22316997, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[3-chloromethyl-4-(methylsulfonyl)phenyl]-5-[4-(2-furyl)phenyl]-3-(trifluoromethyl)-1H-pyrazole from step 1 (70 mg, 0.15 mmol) in THF (3.0 mL), methylamine (5.0 ml, 10 mmol, 2.0 M in THF) and K2CO3 (200 mg, 1.5 mmol) was added at room temperature and stirred for 1 hour. The mixture was concentrated and ethyl acetate (30 mL) was added, dried over MgSO4, and concentrated in vacuo. The solid was dissolved in 10% methanolic HCl (10 mL), and volatiles were removed by evaporation. The residual solid was recrystallized from ethanol to give the title compound (45 mg, 59%).

Workup

  1. concentrationThe mixture was concentrated
  2. additionethyl acetate (30 mL) was added
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. dissolutionThe solid was dissolved in 10% methanolic HCl (10 mL)
  6. customvolatiles were removed by evaporation
  7. customThe residual solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-325700c0bcbe446dbd755dce5978fa6d
Source dataset
uspto-grants-2005_09
Patent number
US06949536B2

Reaction notes

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