2,4,6-Trimethylpyridine → HCID 20775748, compound

HRID 1015619Notes

Reaction equation

HRID 1015619 reaction equation
[C:1]1(C)[C:2]([S:7]([NH:10][C:11]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][C:19](C)=[CH:18][CH:17]=3)[S:13][C:12]=2[C:23]([OH:25])=O)(=[O:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[CH3:27]N(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[CH3:52][O:53][C:54](=[O:57])[CH2:55][NH2:56].N1C(C)=CC(C)=CC=1C>CN(C)C=O>[CH3:52][O:53][C:54](=[O:57])[CH2:55][NH:56][C:23]([C:12]1[S:13][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:15][C:11]=1[NH:10][S:7]([C:2]1[CH:1]=[CH:6][C:5]([CH3:27])=[CH:4][CH:3]=1)(=[O:9])=[O:8])=[O:25]

Participants

6

Reactant 4

HCID 79532,4,6-TrimethylpyridineHCID 122755Glycine methyl ester hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22496172HCID 22496172, compound

Product 1

HCID 20775748HCID 20775748, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-phenyl-3-(toluene-4-sulfonylamino)-thiophene-2-carboxylic acid (prepared according to example 2) (50 mg, 0.134 mmol) in anhydrous dimethylformamide (1.4 ml) were added HATU 152 mg, 0.402 mmol), glycine methyl ester hydrochloride (20 mg, 0.161 mmol) followed by collidine (124 μl, 0.938 mmol). The mixture was stirred at room temperature for 1 hour, concentrated and pre-absorbed on SiO2. Purification chromatography (hexane to hexane:ethyl acetate; 6:4 to dichloromethane: methanol; 95:5) gave 47 mg of a mixture of {[5-Phenyl-3-(toluene-4-sulfonylamino)-thiophene-2-carbonyl]-amino}-acetic acid methyl ester and collidine. 1H NMR (CDCl3, 400 MHz) 7.76-7.73 (m, 2H), 7.61 (s, 1H), 7.57-7.54 (m, 2H), 7.42-7.36 (m, 3H), 7.24-7.22 (m, 2H), 6.19-6.17 (m, 1H), 4.14-4.12 (m, 2H), 3.79 (s, 3H), 2.35 (s, 3H).

Workup

  1. concentrationconcentrated
  2. custompre-absorbed on SiO2
  3. customPurification chromatography (hexane to hexane:ethyl acetate; 6:4 to dichloromethane: methanol; 95:5)

Sources & evidence

ORD record
ord-6453b58a1dba450d89f630e2ba57ae5f
Source dataset
uspto-grants-2011_07
Patent number
US07985769B2

Reaction notes

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