Pyrazole-1-carboxamidine monohydrochloride → HCID 178429046, compound

HRID 1977928Notes

Reaction equation

HRID 1977928 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([O:11][C:12]1[CH:13]=[C:14]([CH:21]=[C:22]([CH3:24])[CH:23]=1)[O:15][CH2:16][CH2:17][CH2:18][O:19][NH2:20])(=[O:10])=[O:9].Cl.[N:26]1([C:31](N)=[NH:32])C=CC=N1>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([O:11][C:12]1[CH:13]=[C:14]([CH:21]=[C:22]([CH3:24])[CH:23]=1)[O:15][CH2:16][CH2:17][CH2:18][O:19][NH:20][C:31]([NH2:32])=[NH:26])(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 2734672Pyrazole-1-carboxamidine monohydrochloride2×HCID 11485564HCID 11485564, compound

Product 1

HCID 178429046HCID 178429046, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-[3-(2-chlorophenylsulfonyloxy)-5-methylphenoxy]propoxyamine (0.43 g, 0.0012 mol), as prepared in the preceding step, in anhydrous N,N-dimethylformamide (15 mL) was treated with 1H -pyrazole-1-carboxamidine hydrochloride (0.34 g, 0.0034 mol). The reaction mixture was stirred overnight at ambient temperature. An additional 100 mg of 1H -pyrazole-1-carboxamidine hydrochloride was added, and the reaction mixture was stirred at ambient temperature overnight. The reaction mixture was evaporated to dryness under high vacuum. The residue was treated with acetonitrile, and the resulting crystalline material was collected by filtration and discarded. The filtrate was evaporated to dryness and partitioned between ether and water. The aqueous layer was washed with ether (4×25 mL). The aqueous layer was separated and basified with 2N sodium hydroxide, and the resultant aqueous layer was extracted with ethyl acetate (4×50 mL). The combined ethyl acetate extracts were washed with brine, dried, and evaporated to give 0.46 g of the title compound as an oil. 1H-NMR (300 MHz, CDCl3) δ7.94 (d, J=7.6 Hz, 1H), 7.54-7.62 (m, 2H), 7.34-7.40 (m, 1H), 6.57 (br s, 1H), 6.48 (m, 2H), 5.75 (br m, 2H), 3.96 (t, J=6.2 Hz, 4H), 2.21 (s, 3H), and 2.05 (pentet, J=6.2 Hz, 2H). Mass spectrum (MALDI-TOF, α-cyano-4-hydroxycinnamic acid matrix) calcd. for C17H20ClN3O5S: 4.14.1 (M+H). Found: 4.14.2

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature overnight
  2. customThe reaction mixture was evaporated to dryness under high vacuum
  3. additionThe residue was treated with acetonitrile
  4. filtrationthe resulting crystalline material was collected by filtration
  5. customThe filtrate was evaporated to dryness
  6. custompartitioned between ether and water
  7. washThe aqueous layer was washed with ether (4×25 mL)
  8. customThe aqueous layer was separated
  9. extractionthe resultant aqueous layer was extracted with ethyl acetate (4×50 mL)
  10. washThe combined ethyl acetate extracts were washed with brine
  11. customdried
  12. customevaporated

Sources & evidence

ORD record
ord-7bff21f54be44860b5df427cc339e2cb
Source dataset
uspto-grants-2001_05
Patent number
US06235778B1

Reaction notes

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