Pyrazole-1-carboxamidine monohydrochloride → HCID 178462152, compound

HRID 366084Notes

Reaction equation

HRID 366084 reaction equation
[C:1]1([CH:7]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:8]([NH:10][C@@H:11]([C:16]([NH:18][C@@H:19]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[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:41].[N:42]1([C:47](N)=[NH:48])C=CC=N1>CN(C=O)C>[ClH:41].[C:35]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]([NH:10][C@@H:11]([C:16]([NH:18][C@@H:19]([C:21]2[CH:22]=[CH:23][C:24]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:25][CH:26]=2)[CH3:20])=[O:17])[CH2:12][CH2:13][CH2:14][NH:15][C:47](=[NH:42])[NH2:48])=[O:9])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

4

Reactant 2

HCID 2734672Pyrazole-1-carboxamidine monohydrochlorideHCID 131722092HCID 131722092, compound

Product 1

HCID 178462152HCID 178462152, compoundYield 73.4%

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-(4-benzyloxyphenyl)ethyl]ornithine amide (0.38 g; 0.71 mmol; from step (d) above), 1H-pyrazole-1-carboxamidine monohydrochloride (0.10 g; 0.71 mmol), TEA (0.14 g, 1.42 mmol) and DMF (5 mL), 18 hours reaction time. The resulting solution was concentrated and chromatographed on silica eluting with MeOH:CHCl3 :conc. NH4OH (3:6:1) and converted to the hydrochloride salt to afford the title compound as a white solid (0.32 g).

Workup

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

Sources & evidence

ORD record
ord-4006a67454944f3ab77e83291d6c7e09
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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