Pyrazole-1-carboxamidine monohydrochloride → HCID 178462149, compound

HRID 366088Notes

Reaction equation

HRID 366088 reaction equation
[C:1]1([CH:7]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:8]([NH:10][C@@H:11]([C:16]([NH:18][C@@H:19]([C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=[CH:23][CH:22]=2)[CH3:20])=[O:17])[CH2:12][CH2:13][CH2:14][NH2:15])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:37].[N:38]1([C:43](N)=[NH:44])C=CC=N1>CN(C=O)C>[NH4+:10].[OH-:9].[ClH:37].[C:31]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]([NH:10][C@@H:11]([C:16]([NH:18][C@@H:19]([C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=[CH:23][CH:22]=2)[CH3:20])=[O:17])[CH2:12][CH2:13][CH2:14][NH:15][C:43](=[NH:38])[NH2:44])=[O:9])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 2

HCID 2734672Pyrazole-1-carboxamidine monohydrochlorideHCID 131722099HCID 131722099, compound

Product 2

HCID 14923Ammonium HydroxideHCID 178462149HCID 178462149, compoundYield 154.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared according to the method described in Example 6(e) above from (R)-N2 -(diphenylacetyl)-(R)-N-[1-(1-naphthyl)ethyl]ornithine amide (0.42 g; 0.88 mmol; step (d) above), 1H-pyrazole-1-carboxamidine mono-hydrochloride (0.14 g; 0.88 mmol), TEA (0.18 g; 1.76 mmol) and DMF (8 mL), 18 hours reaction time. The resultant solution was concentrated and chromatographed on silica eluting with MeOH:CHCl3 :conc. NH4OH (3:6:1) to afford the title compound as a white solid (0.38 g).

Workup

  1. customPrepared
  2. concentrationThe resultant solution was concentrated
  3. customchromatographed on silica eluting with MeOH

Sources & evidence

ORD record
ord-2f6a5ae1ff7d4b2dabd20531e507bc83
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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