2,4,6-Trimethylpyridine → HCID 178476722, compound

HRID 1883488Notes

Reaction equation

HRID 1883488 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[C:12]([NH:14][C@@H:15]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:16]([OH:18])=[O:17])=[O:13])=[CH:6][CH:5]=1)(=[NH:3])[NH2:2].Cl.Cl.[NH2:33][C@@H:34]([CH2:38][CH2:39][CH2:40][NH:41][C:42]([NH2:44])=[NH:43])[C:35]([NH2:37])=[O:36].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N1C(C)=CC(C)=CC=1C>CN(C)C=O>[C:16]([OH:18])(=[O:17])[CH3:15].[C:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH:11]([CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[C:12]([NH:14][C@@H:15]([CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[C:16]([NH:33][C@@H:34]([CH2:38][CH2:39][CH2:40][NH:41][C:42]([NH2:44])=[NH:43])[C:35]([NH2:37])=[O:36])=[O:17])=[O:13])=[CH:8][CH:9]=1)(=[NH:2])[NH2:3]

Participants

6

Reactant 4

HCID 79532,4,6-TrimethylpyridineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 54143502HCID 54143502, compoundHCID 178478814HCID 178478814, compound

Product 1

HCID 178476722HCID 178476722, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To [3-(4-carbamimidoyl-phenyl)-2-cyclohexyl-propionylamino]-(S)-cyclohexyl-acetic acid (41 mg, 0.1 mmol, less polar diastereomer, example 1h) and 2-(S)-amino-5-guanidino-pentanoic acid amide dihydrochloride (24.6 mg, 0.1 mmol) in dimethylformamide (5 ml) were added HATU (39 mg, 0.1 mmol) and collidine (24.2 mg, 0.2 mmol) at 0° C. The mixture was stirred for 1 hour and then allowed to warm to room temperature. After evaporation, the residue was purified by chromatography on Sephadex LH20 employing n-butanol (17): glacial acetic acid (1): water (2) as eluent. Pure fractions were combined. The solvent was evaporated, the residue was taken up in water, and the aqueous solution was lyophilized. Yield: 50 mg (74%), MS m/z: 569.5 (M+H)+, 285.4 (M+2H)2+.

Workup

  1. customAfter evaporation
  2. customthe residue was purified by chromatography on Sephadex
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-888f316341b74d0eb5713b8efac97142
Source dataset
uspto-grants-2004_07
Patent number
US06759420B1

Reaction notes

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