2,4,6-Trimethylpyridine → HCID 69759425, compound

HRID 1883491Notes

Reaction equation

HRID 1883491 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].C(OC([N:38]1[CH2:43][CH2:42][CH:41]([CH2:44]CN)[CH2:40][CH2:39]1)=O)(C)(C)C.C[N:48](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:9]=[CH:8][C:7]([CH2:10][CH:11]([CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]2)[C:12]([NH:14][C@@H:15]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:16](=[O:18])[NH:48][CH2:44][CH:41]2[CH2:40][CH2:39][NH:38][CH2:43][CH2:42]2)=[O:13])=[CH:6][CH:5]=1)(=[NH:3])[NH2:2]

Participants

6

Reactant 4

HCID 79532,4,6-TrimethylpyridineHCID 1514258tert-Butyl 4-(2-aminoethyl)piperidine-1-carboxylateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 54143502HCID 54143502, compound

Product 1

HCID 69759425HCID 69759425, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To (S)-[3-(4-carbamimidoyl-phenyl)-2-cyclohexyl-propionylamino]-cyclohexyl-acetic acid (50 mg, 0.12 mmol, less polar diastereomer, example 1 h) and 4-aminoethyl-piperidine-1-carboxylic acid tert-butyl ester (26 mg, 0.12 mmol) in dimethylformamide (5 ml) were added HATU (50 mg, 0.13 mmol) and collidine (16 mg, 0.13 mmol) at 0° C. The mixture was stirred for 1 hour and then allowed to warm to room temperature. The mixture was evaporated and treated with 2 ml of trifluoroacetic acid (containing 10% water) for 2 hours. 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: 45 mg (59%), MS m/z: 510.5 (M+H)+, 255.8 (M+2H)2+.

Workup

  1. custom50 mg, 0.12 mmol, less polar diastereomer, example 1 h
  2. customat 0° C
  3. customThe mixture was evaporated
  4. additiontreated with 2 ml of trifluoroacetic acid (containing 10% water) for 2 hours
  5. customAfter evaporation
  6. customthe residue was purified by chromatography on Sephadex
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-2ac3c88b0aba4abfb955e05ee23b4190
Source dataset
uspto-grants-2004_07
Patent number
US06759420B1

Reaction notes

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