Methanol → HCID 86673354, compound

HRID 517994Notes

Reaction equation

HRID 517994 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:21]=[C:20]([C:22]#[N:23])[C:19]3[N:24]=[N:25][N:26]([CH3:27])[C:18]=3[CH:17]=2)=[CH:12][C:11]=1[C:28]([F:31])([F:30])[F:29].C(N(C(C)C)CC)(C)C.CO>O>[CH3:1][S:2]([O:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:21]=[C:20]([C:22]#[N:23])[C:19]3[N:24]=[N:25][N:26]([CH3:27])[C:18]=3[CH:17]=2)=[CH:12][C:11]=1[C:28]([F:30])([F:29])[F:31])(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 672942706-(4-(2-hydroxyethoxy)-3-(trifluoromethyl)phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile

Product 1

HCID 86673354HCID 86673354, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methanesulfonyl chloride (3.95 ml, 4.53 g) was added dropwise at 0° C. to a solution of 6-(4-(2-hydroxyethoxy)-3-(trifluoromethyl)phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile (5.7 g) and diisopropylethylamine (17.28 ml, 12.79 g). The mixture was stirred at room temperature for 1 hour. 10 ml methanol added and stirred for 5 minutes, followed by cold water (20 ml). Product precipitated, collected by filtration and washed with diethyl ether. Sample dried in the oven to give 2-(4-(4-cyano-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridin-6-yl)-2-(trifluoromethyl)-phenoxy)ethyl methanesulfonate (6.3 g). 1H NMR (DMSO) δ: 8.99 (s, 8.99), 8.48 (m, 2H), 7.53 (d, 1H), 4.60 (m, 4H), 4.46 (s, 3H), 3.24 (s, 3H). MS m/z 442 (M+H).

Workup

  1. stirringstirred for 5 minutes
  2. customProduct precipitated
  3. filtrationcollected by filtration
  4. washwashed with diethyl ether
  5. customSample dried in the oven

Sources & evidence

ORD record
ord-c95f0be07b924b48a8ccee80c055939d
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

Loading…