Lithium Hydroxide → HCID 57870819, compound

HRID 1363048Notes

Reaction equation

HRID 1363048 reaction equation
ClC1C=CC(S(Cl)(=O)=O)=CC=1C(F)(F)F.COC(C1C(N)=CC=CN=1)=O.ClC1C=CC(S(NC2C(C#N)=NC=C(C)C=2)(=O)=O)=CC=1C(F)(F)F.[Cl:51][C:52]1[CH:57]=[CH:56][C:55]([S:58]([NH:61][C:62]2[C:63]([C:69]([OH:71])=[O:70])=[N:64][CH:65]=[C:66](C)[CH:67]=2)(=[O:60])=[O:59])=[CH:54][C:53]=1[C:72]([F:75])([F:74])[F:73].[Li+].[OH-]>N1C=CC=CC=1.C1COCC1>[Cl:51][C:52]1[CH:57]=[CH:56][C:55]([S:58]([NH:61][C:62]2[C:63]([C:69]([OH:71])=[O:70])=[N:64][CH:65]=[CH:66][CH:67]=2)(=[O:59])=[O:60])=[CH:54][C:53]=1[C:72]([F:74])([F:73])[F:75]

Participants

8

Reactant 5

HCID 3939Lithium HydroxideHCID 27807194-Chloro-3-(trifluoromethyl)benzenesulfonyl ChlorideHCID 9898880Methyl 3-aminopicolinateHCID 57870807HCID 57870807, compoundHCID 57870815HCID 57870815, compound

Product 1

HCID 57870819HCID 57870819, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

Prepared from 0.60 g (2.17 mmol) of 4-chloro-3-trifluoromethyl-benzenesulfonyl chloride and 0.30 g (1.97 mmol) of 3-amino-pyridine-2-carboxylic acid methyl ester in 3 mL pyridine using the procedure used to prepare 4-chloro-N-(2-cyano-5-methylpyridine-3-yl)-3-(trifluoromethyl)benzenesulfonamide in the preparation of Intermediate 6. The solvent was switched to THF, followed by the addition of 1 M aqueous LiOH and the mixture stirred for 1 hour. The pH of the mixture was adjusted to neutral and the product was extracted with ethyl acetate. LC-MSD, m/z for C13H8ClF3N2O4S [M+H]+=380.9, 383.0; HPLC retention time: 1.8 minutes.

Workup

  1. extractionwas extracted with ethyl acetate

Sources & evidence

ORD record
ord-7f23a771871d4b44bb18b8257649df4c
Source dataset
uspto-grants-2011_02
Patent number
US07884110B2

Reaction notes

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