2,4,6-Trimethylpyridine → HCID 58866206, compound

HRID 1364969Notes

Reaction equation

HRID 1364969 reaction equation
[CH3:1][Si:2]([CH3:19])([CH3:18])[CH2:3][CH2:4][O:5][C:6]([NH:8][C:9]1([C:15]([OH:17])=O)[CH2:14][O:13][CH2:12][O:11][CH2:10]1)=[O:7].[CH2:20]([O:22][C:23](=[O:33])[CH:24]=[CH:25][C:26]1[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=1)[CH3:21].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=NC2N(O)N=NC=2C=1.N1C(C)=CC(C)=CC=1C>CS(C)=O>[CH2:20]([O:22][C:23](=[O:33])/[CH:24]=[CH:25]/[C:26]1[CH:27]=[CH:28][C:29]([NH:32][C:15]([C:9]2([NH:8][C:6]([O:5][CH2:4][CH2:3][Si:2]([CH3:1])([CH3:19])[CH3:18])=[O:7])[CH2:10][O:11][CH2:12][O:13][CH2:14]2)=[O:17])=[CH:30][CH:31]=1)[CH3:21]

Participants

7

Reactant 5

HCID 79532,4,6-TrimethylpyridineHCID 97826Ethyl 3-(4-aminophenyl)acrylateHCID 181649HOAtHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×HCID 21105263HCID 21105263, compound

Product 1

HCID 58866206HCID 58866206, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

5-(2-trimethylsilanyl-ethoxycarbonylamino)-1,3-dioxane-5-carboxylic acid from above (0.050 g, 0.17 mmol), ethyl-4-aminocinnamate (0.036 g, 0.19 mmol), HATU (0.098 g, 0.26 mmol), HOAt (0.035 g, 0.26 mmol) and 2,4,6-collidine (0.062 mL, 0.51 mmol) were combined in anhydrous DMSO (1 mL). The solution was warmed to 60° C. and stirred for 6 h before another 1.5 equivalents of HATU was added and stirring was continued for another 2 hours to ensure complete consumption of the acid. The reaction mixture was diluted with dichloromethane and washed with 1N HCl (×2). The organic phase was dried with MgSO4, filtered and concentrated. The residue was subjected to flash chromatography to afford 0.043 g (54%) of the protected amide derivative as a yellow oil.

Workup

  1. additionwas added
  2. customconsumption of the acid
  3. additionThe reaction mixture was diluted with dichloromethane
  4. washwashed with 1N HCl (×2)
  5. dry with materialThe organic phase was dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4a423f7c5c5041afa6cb3983cab69ff7
Source dataset
uspto-grants-2011_02
Patent number
US07888363B2

Reaction notes

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