Methanesulfonyl chloride → 3-(4-(4-cyano-1-methyl-1H-benzo[d][1,2,3]triazol-6-yl)-2-(trifluoromethyl)phenoxy)propyl methanesulfonate

HRID 517987Notes

Reaction equation

HRID 517987 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2N=[C:21]([C:23]#[N:24])[C:20]3[N:25]=[N:26][N:27]([CH3:28])[C:19]=3[CH:18]=2)=[CH:13][C:12]=1[C:29]([F:32])([F:31])[F:30].[CH:33](N(C(C)C)CC)(C)C>C(Cl)Cl>[CH3:1][S:2]([O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:33]=[C:21]([C:23]#[N:24])[C:20]3[N:25]=[N:26][N:27]([CH3:28])[C:19]=3[CH:18]=2)=[CH:13][C:12]=1[C:29]([F:30])([F:32])[F:31])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 533303906-(4-(3-hydroxypropoxy)-3-(trifluoromethyl)phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile

Product 1

HCID 866733533-(4-(4-cyano-1-methyl-1H-benzo[d][1,2,3]triazol-6-yl)-2-(trifluoromethyl)phenoxy)propyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulphonyl chloride (6.29 g) was added dropwise to a solution of 6-(4-(3-hydroxypropoxy)-3-(trifluoromethyl)phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]-pyridine-4-carbonitrile (10.34 g) and diisopropylethylamine (22.7 ml) in DCM (300 ml) at 0° C. The mixture was stirred at room temperature for 2 hours. The DCM was removed under reduced pressure, MeOH and water were added to the residue and the solid was collected by filtration to give the expected product (11.56 g). 1H NMR (DMSO) δ: 8.96 (s, 1H), 8.49 (d, 1H), 8.46 (s, 1H), 7.51 (d, 1H), 4.46 (s, 3H), 4.39 (t, 2H), 4.34 (t, 2H), 3.18 (s, 3H), 2.21 (quin, 2H).

Workup

  1. customThe DCM was removed under reduced pressure, MeOH and water
  2. additionwere added to the residue
  3. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-b31621517638454e800bfb4ae6b315b7
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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