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

HRID 2193903Notes

Reaction equation

HRID 2193903 reaction equation
[C:1]1([C:7]2[S:11][C:10]([C:12](O)=[O:13])=[C:9]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[CH3:51][O:52][C:53](=[O:56])[CH2:54][NH2:55].N1C(C)=CC(C)=CC=1C>CN(C)C=O>[CH3:51][O:52][C:53](=[O:56])[CH2:54][NH:55][C:12]([C:10]1[S:11][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:8][C:9]=1[NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)(=[O:18])=[O:17])=[O:13]

Participants

6

Reactant 4

HCID 79532,4,6-TrimethylpyridineHCID 122755Glycine methyl ester hydrochlorideHCID 503523HCID 503523, compoundHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

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-4e615431259849689e8733892c33bf92
Source dataset
uspto-grants-2012_12
Patent number
US08329924B2

Reaction notes

Loading…