Pyrazole-1-carboxamidine monohydrochloride → HCID 178489635, compound

HRID 1977934Notes

Reaction equation

HRID 1977934 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([O:12][C:13]1[CH:14]=[C:15]([CH:22]=[C:23]([CH3:25])[CH:24]=1)[O:16][CH2:17][CH2:18][CH2:19][O:20][NH2:21])(=[O:11])=[O:10].Cl.[N:27]1([C:32](N)=[NH:33])C=CC=N1>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([O:12][C:13]1[CH:14]=[C:15]([CH:22]=[C:23]([CH3:25])[CH:24]=1)[O:16][CH2:17][CH2:18][CH2:19][O:20][NH:21][C:32]([NH2:33])=[NH:27])(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 2734672Pyrazole-1-carboxamidine monohydrochloride2×HCID 227225423-[3-(2-Methoxyphenylsulfonyloxy)-5-methylphenoxy]propoxyamine

Product 1

HCID 178489635HCID 178489635, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-[3-(2-methoxyphenylsulfonyloxy)-5-methylphenoxy]propoxyamine (74 mg, 0.20 mmol, prepared in the preceding step) and 1H-pyrazole-1-carboxamidine hydrochloride (60 mg, 0.41 mmol) in anhydrous N,N-dimethylformamide (2 mL) was stirred at ambient temperature overnight. Additional 1H-pyrazole-1-carboxamidine hydrochloride (30 mg, 0.20 mmol) was added, and the reaction was stirred at ambient temperature for 3 days. N,N-Dimethylformamide was removed in vacuo, then the residue was treated with acetonitrile. The mixture was filtered to remove excess 1H-pyrazole-1-carboxamidine hydrochloride, and the filtrate was concentrated in vacuo. The residual oil was partitioned between diethyl ether (10 mL) and water (10 mL). The aqueous layer was washed with diethyl ether (2×10 mL), adjusted to pH 8 with 2N NaOH, and extracted with ethyl acetate (2×10 mL). The ethyl acetate extracts were washed with pH 7 buffer (2×15 mL) and brine (15 mL), dried over Na2SO4, filtered, and evaporated to give the title compound (64 mg, 78%) as a colorless oil. 1H-NMR (300 MHz, DMSO-d6) δ7.76 (ddd, 1H, J=8.4, 7.4, 1.8 Hz), 7.69 (dd, 1H, J=7.9, 1.6 Hz), 7.37 (d, 1H, J=7.7 Hz), 7.09 (dt, 1H, J=7.9, 1.0 Hz), 6.69 (s, 1H), 6.47 (s, 1H), 6.33 (t, 1H, J=2.1 Hz), 4.00 (s, 3H), 3.92 (t, 2H, J=6.5 Hz), 3.70 (t, 2H, J=6.1 Hz), 2.20 (s, 3H), 1.88 (pentet, 2H, J=6.3 Hz). Mass spectrum (MALDI-TOF, α-cyano-4-hydroxycinnamic acid matrix) calcd. for C18H23N3O6S: 410.1 (M+H), 432.1 (M+Na). Found: 410.1, 432.6.

Workup

  1. stirringthe reaction was stirred at ambient temperature for 3 days
  2. customN,N-Dimethylformamide was removed in vacuo
  3. additionthe residue was treated with acetonitrile
  4. filtrationThe mixture was filtered
  5. customto remove excess 1H-pyrazole-1-carboxamidine hydrochloride
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe residual oil was partitioned between diethyl ether (10 mL) and water (10 mL)
  8. washThe aqueous layer was washed with diethyl ether (2×10 mL)
  9. extractionextracted with ethyl acetate (2×10 mL)
  10. washThe ethyl acetate extracts were washed with pH 7 buffer (2×15 mL) and brine (15 mL)
  11. dry with materialdried over Na2SO4
  12. filtrationfiltered
  13. customevaporated

Sources & evidence

ORD record
ord-0b87f734c347406fa77488479f4c698d
Source dataset
uspto-grants-2001_05
Patent number
US06235778B1

Reaction notes

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