3,5-Dimethyl-1H-pyrazole-1-carboxamidine mononitrate → HCID 176525553, compound

HRID 1757086Notes

Reaction equation

HRID 1757086 reaction equation
[NH2:1][CH2:2][CH2:3][O:4]/[N:5]=[CH:6]/[C@H:7]1[CH2:12][CH2:11][C@:10]2([OH:27])[C@H:13]3[C@H:23]([CH2:24][CH2:25][C@:8]12[CH3:9])[C@:21]1([CH3:22])[C@@H:16]([CH2:17][C@@H:18]([OH:26])[CH2:19][CH2:20]1)[CH2:15][CH2:14]3.[N+]([O-])(O)=O.[C:32](N1C(C)=CC(C)=N1)(=[NH:34])[NH2:33]>C(O)C>[NH:1]([CH2:2][CH2:3][O:4]/[N:5]=[CH:6]/[C@H:7]1[CH2:12][CH2:11][C@:10]2([OH:27])[C@H:13]3[C@H:23]([CH2:24][CH2:25][C@:8]12[CH3:9])[C@:21]1([CH3:22])[C@@H:16]([CH2:17][C@@H:18]([OH:26])[CH2:19][CH2:20]1)[CH2:15][CH2:14]3)[C:32]([NH2:34])=[NH:33]

Participants

4

Reactant 2

HCID 1981863,5-Dimethyl-1H-pyrazole-1-carboxamidine mononitrateHCID 10738454HCID 10738454, compound

Product 1

HCID 176525553HCID 176525553, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 0.95 g of (E)-17β-(2-aminoethoxyimino)methyl-5β-androstane-3β,14β-diol (I-ab) and 1.05 g of 1-amidino-3,5-dimethylpyrazole nitrate in 20 ml of ethanol was heated at reflux for 10 hrs. The solution was evaporated to dryness under reduced pressure and the crude product was purified by flash-chromatography (SiO2) using chloroform/methanol/28% ammonium hydroxide 78/20/2 as eluant; the fractions containing the title compound were collected and evaporated to dryness under reduced pressure. The residue was ground with di-iso-propyl ether/ethanol to give 0.38 g of the title compound (I-ag), as a nitrate, white solid.

Workup

  1. temperatureat reflux for 10 hrs
  2. customThe solution was evaporated to dryness under reduced pressure
  3. customthe crude product was purified by flash-chromatography (SiO2)
  4. additionthe fractions containing the title compound
  5. customwere collected
  6. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-779ff4d5ff8845fb951f8b419db60671
Source dataset
uspto-grants-1995_08
Patent number
US05444055

Reaction notes

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