Pyrazole-1-carboxamidine monohydrochloride → HCID 178429049, compound

HRID 1059467Notes

Reaction equation

HRID 1059467 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]2[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]2)(=[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]2[CH2:28][CH2:29][N:30]([CH3:33])[CH2:31][CH2:32]2)(=[O:25])=[O:26])(=[O:17])=[O:16])[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 22722415HCID 22722415, compound

Product 1

HCID 178429049HCID 178429049, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-[5-Methyl-3-(2-(4-methylpiperazinylsulfonyl)phenylsulfonylox)phenoxy]propoxy guanidine hydrochloride: A mixture of 3-[5-methyl-3-(2-(4-methylpiperazinylsulfonyl)phenylsulfonyloxy) phenoxy]propoxyamine (113 mg, 0.23 mmol), as prepared in the previous step, and 1H-pyrazole-1-carboxamidine hydrochloride (62 mg, 0.42 mmol) in anhydrous N,N-dimethylformamide (10 mL) was stirred at room temperature under nitrogen (balloon) for 18 hours. The solution was concentrated under high vacuum with heating and the residue was purified by flash chromatography (10% to 20% methanol in dichloromethane), then dissolved in dichloromethane, filtered and concentrated to give the title compound (105 mg, 80%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.20 (m, 2H), 7.83 (td, 1H, J=7.7, 1.3 Hz), 7.70 (td, 1H, J=7.7, 1.2 Hz), 6.59 (m, 2H), 6.52 (m, 1H), 6.28 (m, 3H), 4.04 (t, 2H, J=5.8 Hz), 3.96 (t, 2H, J=5.8 Hz), 3.43 (m, 4H), 2.33 (s, 3H), 2.23 (s, 3H), 2.00 (m, 2H). Mass spectrum (MALDI-TOF, α-cyano-4-hydroxycinnamic acid matrix) calcd. for C22H31N5O7S2: 542.2 (M+H), 564.2 (M+Na). Found: 542.3, 564.3.

Workup

  1. concentrationThe solution was concentrated under high vacuum
  2. temperaturewith heating
  3. customthe residue was purified by flash chromatography (10% to 20% methanol in dichloromethane)
  4. dissolutiondissolved in dichloromethane
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c64763e631fc48bf8b39a4286c34af95
Source dataset
uspto-grants-2003_02
Patent number
US06518310B2

Reaction notes

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