Potassium Carbonate → HCID 72550657, compound

HRID 590531Notes

Reaction equation

HRID 590531 reaction equation
Cl.[CH3:2][NH:3][OH:4].C(=O)([O-])[O-].[K+].[K+].[F:11][C:12]([F:32])([F:31])[C:13]1[CH:14]=[C:15]([C:19]2[S:23][C:22]3[CH2:24][CH2:25][CH2:26]/[C:27](=[N:28]\[C:29]#[N:30])/[C:21]=3[CH:20]=2)[CH:16]=[CH:17][CH:18]=1>CO>[CH3:2][N:3]1[C:29]([NH2:30])=[N:28][C:27]2([C:21]3[CH:20]=[C:19]([C:15]4[CH:16]=[CH:17][CH:18]=[C:13]([C:12]([F:11])([F:31])[F:32])[CH:14]=4)[S:23][C:22]=3[CH2:24][CH2:25][CH2:26]2)[O:4]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77906N-methylhydroxylamine hydrochlorideHCID 178511969HCID 178511969, compound

Product 1

HCID 72550657HCID 72550657, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methylhydroxylamine hydrochloride (23 mg, 0.28 mmol) in methanol (2 mL) was added potassium carbonate (44 mg, 0.32 mmol) followed by (E)-N-(2-(3-(trifluoromethyl)phenyl)-6,7-dihydrobenzo[b]thiophen-4(5H)-ylidene)cyanamide (50 mg, 0.16 mmol). The reaction mixture was stirred at room temperature for 1 hr. The mixture was concentrated in vacuo and the crude residue partitioned between dichloromethane and water. The product was extracted into dichloromethane (×3). The organic extracts were combined, dried (MgSO4) and concentrated under reduced pressure. The crude residue was purified using preparative HPLC to give the title compound as yellow solid (34.2 mg, 58%). (regioisomeric mix with 2′-methyl-2-(3-(trifluoromethyl)phenyl)-6,7-dihydro-2′H, 5H-spiro[benzo[b]thiophene-4,3′-[1,2,4]oxadiazol]-5′-amine). 1H NMR δ (ppm)(DMSO-d6): 7.87-7.80 (2H, m), 7.64-7.58 (2H, m), 7.34 (1H, s), 6.12 (2H, s), 2.94 (3H, s), 2.80-2.60 (2H, m), 1.93-1.80 (3H, m), 1.80-1.69 (1H, m). HPLC (Method a) Rt 8.05 (min) m/z 368 (MH+).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe crude residue partitioned between dichloromethane and water
  3. extractionThe product was extracted into dichloromethane (×3)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified

Sources & evidence

ORD record
ord-fa3cec3e1da84ec980077d70347e7bce
Source dataset
uspto-grants-2016_01
Patent number
US09233982B2

Reaction notes

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