Chloromethyl Methyl Ether → 3-[(4-Chloro-3-trifluoromethyl-benzenesulfonyl)-methoxymethyl-amino]-pyridine-2-carboxylic acid methoxy-methyl-amide

HRID 1054503Notes

Reaction equation

HRID 1054503 reaction equation
CON(C)C(C1C(NS(C2C=CC(Cl)=C(C(F)(F)F)C=2)(=O)=O)=CC=CN=1)=O.C(=O)([O-])[O-].[K+].[K+].COCCl.[CH3:38][O:39][N:40]([CH3:68])[C:41]([C:43]1[C:48]([N:49]([CH2:64][O:65][CH3:66])[S:50]([C:53]2[CH:58]=[CH:57][C:56]([Cl:59])=[C:55]([C:60]([F:63])([F:62])[F:61])[CH:54]=2)(=[O:52])=[O:51])=[CH:47][C:46](Cl)=[CH:45][N:44]=1)=[O:42]>C1COCC1>[CH3:38][O:39][N:40]([CH3:68])[C:41]([C:43]1[C:48]([N:49]([S:50]([C:53]2[CH:58]=[CH:57][C:56]([Cl:59])=[C:55]([C:60]([F:63])([F:62])[F:61])[CH:54]=2)(=[O:51])=[O:52])[CH2:64][O:65][CH3:66])=[CH:47][CH:46]=[CH:45][N:44]=1)=[O:42]

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 578708273-(4-Chloro-3-trifluoromethyl-benzenesulfonylamino)-pyridine-2-carboxylic acid methoxy-methyl-amideHCID 579421195-Chloro-3-[(4-chloro-3-trifluoromethyl-benzenesulfonyl)-methoxymethyl-amino]-pyridine-2-carboxylic acid methoxy-methyl-amide

Product 1

HCID 578708053-[(4-Chloro-3-trifluoromethyl-benzenesulfonyl)-methoxymethyl-amino]-pyridine-2-carboxylic acid methoxy-methyl-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared from 1.05 g (2.48 mmol) of 3-(4-chloro-3-trifluoromethyl-benzenesulfonylamino)-pyridine-2-carboxylic acid methoxy-methyl-amide, 1.71 g of potassium carbonate and 566 μL of methoxymethyl chloride in 7 mL THF using procedure used in the preparation of Intermediate 12. Yield: 420 mg of a white solid. LC-MSD, m/z for C17H17ClF3N3O5S [M+Na]+=490.0, 491.9; HPLC retention time: 2.5 minutes.

Sources & evidence

ORD record
ord-19741808efd4488ead0e1089d0773574
Source dataset
uspto-grants-2016_07
Patent number
US09394307B2

Reaction notes

Loading…