Triethylamine → HCID 178462148, compound

HRID 366037Notes

Reaction equation

HRID 366037 reaction equation
[C:1]1([CH:7]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:8]([NH:10][C@H:11]([C:16]([NH:18][C@@H:19]([C:21]2[CH:26]=[CH:25][C:24]([Br:27])=[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:34].[N:35]1([C:40](N)=[NH:41])C=CC=N1.C(N(CC)CC)C.CCN(C(C)C)C(C)C>CN(C)C=O>[ClH:34].[C:1]1([CH:7]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:8]([NH:10][C@H:11]([C:16]([NH:18][C@@H:19]([C:21]2[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][CH:22]=2)[CH3:20])=[O:17])[CH2:12][CH2:13][CH2:14][NH:15][C:40](=[NH:35])[NH2:41])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 81531DiisopropylethylamineHCID 2734672Pyrazole-1-carboxamidine monohydrochlorideHCID 86755903HCID 86755903, compound

Product 1

HCID 178462148HCID 178462148, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared according to the method described in Example 2(f) above from (R)-N2 -(diphenylacetyl)-(S)-N-[1-(4-bromophenyl)ethyl]ornithine amide (free base; 0.20 g; 0.39 mmol; from step (d) above), 1H-pyrazole-1-carboxamidine mono hydrochloride (0.06 g; 0.39 mmol), triethylamine (0.08 g; 0.78 mmol; instead of DiPEA) and dimethyl formamide (1 mL), 5 hours reaction time. The solution was concentrated under vacuum and the crude product chromatographed on silica gel eluting with MeOH:CHCl3 :ammonium hydroxide (3:6:1). Conversion of the eluted compound to the hydrochloride salt gave the title compound as a white solid (0.17 g).

Workup

  1. customPrepared
  2. concentrationThe solution was concentrated under vacuum
  3. customthe crude product chromatographed on silica gel eluting with MeOH:CHCl3 :ammonium hydroxide (3:6:1)

Sources & evidence

ORD record
ord-d8566f6d9c1c46ce980a50434f7ca967
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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