2,4,6-Trimethylpyridine → HCID 70110228, compound

HRID 352248

Reaction equation

HRID 352248 reaction equation
[NH2:1][CH:2]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:3]([NH:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH:8]([N:12]2[C:21]3[CH:20]=[CH:19][CH:18]=[C:17]([Cl:22])[C:16]=3[C:15]3=[N:23][O:24][C:25]([CH3:26])=[C:14]3[C:13]2=[O:27])[CH2:7]1)=[O:4].Cl.[CH3:35][N:36]1[CH2:41][CH2:40][CH:39]([C:42](O)=[O:43])[CH2:38][CH2:37]1.Cl.CN(C)CCCN=C=NCC.CC1C=C(C)C=C(C)N=1.ON1C2N=CC=CC=2N=N1>CN(C)C=O.C(OCC)(=O)C.O.C([O-])(O)=O.[Na+]>[Cl:22][C:17]1[C:16]2[C:15]3[C:14](=[C:25]([CH3:26])[O:24][N:23]=3)[C:13](=[O:27])[N:12]([CH:8]3[CH2:9][CH2:10][CH2:11][CH:6]([NH:5][C:3]([CH:2]([NH:1][C:42]([CH:39]4[CH2:40][CH2:41][N:36]([CH3:35])[CH2:37][CH2:38]4)=[O:43])[C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)=[O:4])[CH2:7]3)[C:21]=2[CH:20]=[CH:19][CH:18]=1

Participants

10

Reactant 5

HCID 79532,4,6-TrimethylpyridineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27600434-Piperidinecarboxylic acid, 1-methyl-, hydrochloride (1:1)HCID 22713739HCID 22713739, compound

Product 1

HCID 70110228HCID 70110228, compoundYield 74%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A product from Example 638 (50 mg; 0.108 mmol) was dissolved in anhydrous dimethylformamide (10 mL) under a nitrogen atmosphere, mixed with 1-methyl-piperidine-4-carboxylic acid hydrochloride (58.0 mg; 0.323 mmol; 3 equiv), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (61.8 mg; 0.323 mmol; 3 equiv), 2,4,6-trimethylpyridine (86 μL; 0.645 mmol; 6 equiv), and 1-hydroxy-7-azabenzotriazole (43.9 mg; 0.323 mmol; 3 equiv), and stirred overnight at room temperature. The reaction solution was diluted with 2 volumes ethyl acetate, 10 volumes water, and 1 volume saturated NaHCO3(aq). The organic layer was separated and then washed with saturated NaCl(aq), dried over Na2SO4(S), filtered, and concentrated in vacuo. The resulting material was purified by radial chromatography on a 2 mm thick silica gel rotor with a 2% then 4% methanol/dichloromethane (v/v) mobile phase and finally a 2% methanol/0.5% triethylamine/dichloromethane (v/v/v) mobile phase. The desired product was isolated as a white solid in 74% yield (47 mg).

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated NaCl(aq)
  3. dry with materialdried over Na2SO4(S)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting material was purified by radial chromatography on a 2 mm thick silica gel rotor with a 2%

Sources & evidence

ORD record
ord-f916f7e25a7549a4a29505374dfffe9e
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Linked notes

Loading…