Hydrochloric Acid → HCID 69893658, compound

HRID 1290649Notes

Reaction equation

HRID 1290649 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([OH:9])=O)=[CH:5][C:4]([N+:10]([O-:12])=[O:11])=[N:3]1.S(Cl)([Cl:15])=O.Cl.Cl.[CH3:19][N:20]1[CH:24]=[C:23]([NH:25][C:26]([C:28]2[N:29]([CH3:34])[CH:30]=[C:31]([NH2:33])[CH:32]=2)=[O:27])[CH:22]=[C:21]1[C:35]([NH:37][CH2:38][CH2:39][C:40]([NH2:42])=[NH:41])=[O:36].C(=O)(O)[O-].[Na+].Cl>C1C=CC=CC=1.O1CCOCC1.O>[ClH:15].[CH3:19][N:20]1[CH:24]=[C:23]([NH:25][C:26]([C:28]2[N:29]([CH3:34])[CH:30]=[C:31]([NH:33][C:7]([C:6]3[N:2]([CH3:1])[N:3]=[C:4]([N+:10]([O-:12])=[O:11])[CH:5]=3)=[O:9])[CH:32]=2)=[O:27])[CH:22]=[C:21]1[C:35]([NH:37][CH2:38][CH2:39][C:40]([NH2:42])=[NH:41])=[O:36]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 5200387AKOS B024347HCID 14486451HCID 14486451, compound

Product 1

HCID 69893658HCID 69893658, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 0.55 g of 1-methyl-3-nitropyrazole-5-carboxylic acid (prepared as in reported in Example 8) in 10 ml of benzene were added 2 ml of thionyl chloride. The mixture was refluxed for one hour and the solvent evaporated in vacuo to yield a solid residue which was dissolved in 10 ml of dioxane and added in small portions to a solution of 1 g of β-[1-methyl-4-[1-methyl-4-aminopyrrole-2-carboxamido]pyrrole-2-carboxamido]propionamidine, dihydrochloride (prepared as reported in J. Med. Chem. 32,774-778,1989) and 0.2 g of sodium bicarbonate in 10 ml of water. The mixture was stirred for one hour and then brought to pH 4-5 with 10% hydrochloric acid. The Solvent was evaporated in vacuo and the solid residue chromatographed on silica gel eluting whit a mixture methylene chloride-methanol (80:20 by volume), yielding 0.7 g of β-[1-methyl-4-[1-methyl-4-[1-methyl-3-nitropyrazole-5-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]propionamidine, hydrochloride.

Workup

  1. temperatureThe mixture was refluxed for one hour
  2. customthe solvent evaporated in vacuo
  3. customto yield a solid residue which
  4. customThe Solvent was evaporated in vacuo
  5. customthe solid residue chromatographed on silica gel eluting whit a mixture methylene chloride-methanol (80:20 by volume)

Sources & evidence

ORD record
ord-845ea9e9c6ca4ea287e6cffccd096778
Source dataset
uspto-grants-1998_05
Patent number
US05753629

Reaction notes

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