Pyrazole-1-carboxamidine monohydrochloride → HCID 178429057, compound

HRID 1977974Notes

Reaction equation

HRID 1977974 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([O:14][S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[S:24]([N:27]([CH3:33])[CH2:28][CH2:29][N:30]([CH3:32])[CH3:31])(=[O:26])=[O:25])(=[O:17])=[O:16])[CH:5]=[C:6]([CH:13]=1)[O:7][CH2:8][CH2:9][CH2:10][O:11][NH2:12].[ClH:34].[N:35]1([C:40](N)=[NH:41])C=CC=N1>CN(C)C=O>[ClH:34].[CH3:1][C:2]1[CH:3]=[C:4]([O:14][S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[S:24]([N:27]([CH3:33])[CH2:28][CH2:29][N:30]([CH3:31])[CH3:32])(=[O:26])=[O:25])(=[O:16])=[O:17])[CH:5]=[C:6]([CH:13]=1)[O:7][CH2:8][CH2:9][CH2:10][O:11][NH:12][C:40]([NH2:41])=[NH:35]

Participants

4

Reactant 2

HCID 2734672Pyrazole-1-carboxamidine monohydrochlorideHCID 22722426HCID 22722426, compound

Product 1

HCID 178429057HCID 178429057, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-[5-methyl-3-(2-(N-methyl-N-(2-(N,N-dimethylamino)ethyl)aminosulfonyl)phenylsulfonyloxy)phenoxy]propoxyamine (94 mg, 0.19 mmol) and 1H-pyrazole-1-carboxamidine hydrochloride (57 mg, 0.39 mmol), in N,N-dimethylformamide (8 mL) was stirred at room temperature for 18 hours then concentrated in vacuo. The residue was dissolved in acetonitrile, filtered, and the filtrate concentrated to an oil. This was dissolved in dilute HCl (pH 3), washed with diethyl ether, basified with aqueous NaHCO3, and extracted with CH2Cl2. The CH2Cl2 layer was washed with pH 7 buffer and brine, dried over Na2SO4 and filtered. The filtrate was acidified with HCl-methanol and concentrated giving the title compound as a white solid (100 mg, 92%). 1H NMR (300 MHz, CDCl3) δ8.20 (m, 2H), 7.93 (td, 1H, J=7.7, 1.4 Hz), 7.78 (td, 1H, J=7.7, 1.2 Hz), 6.62 (m, 2H), 6.51 (t, 1H, J=2.2 Hz), 4.05 (t, 2H, J=6.1 Hz), 3.99 (t, 2H, J=6.0 Hz), 3.87 (t, 2H, J=6.9 Hz), 3.44 (t, 2H, J=6.9 Hz), 3.04 (s, 3H), 2.96 (s, 6H), 2.27 (s, 3H), 2.10 (m, 2H). Mass spectrum (MALDI-TOF, α-cyano-4-hydroxycinnamic acid matrix) calcd. for C22H33N5O7S2: 544.2 (M+H). Found: 544.0.

Workup

  1. concentrationthen concentrated in vacuo
  2. dissolutionThe residue was dissolved in acetonitrile
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated to an oil
  5. dissolutionThis was dissolved in dilute HCl (pH 3)
  6. washwashed with diethyl ether
  7. extractionextracted with CH2Cl2
  8. washThe CH2Cl2 layer was washed with pH 7 buffer
  9. dry with materialbrine, dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-c6385277ff664ee8957e53a1b65b15f3
Source dataset
uspto-grants-2001_05
Patent number
US06235778B1

Reaction notes

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