Sodium Hydroxide → HCID 178457029, compound

HRID 1655606Notes

Reaction equation

HRID 1655606 reaction equation
[CH2:1]([N:4]([C:42]1[C:47]([C:48]([O:50]CC)=[O:49])=[CH:46][CH:45]=[C:44]([C:53]([F:56])([F:55])[F:54])[N:43]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]2[N:22](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:21]=[N:20][N:19]=2)=[CH:8][CH:7]=1)[CH2:2][CH3:3].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>CO>[CH2:1]([N:4]([C:42]1[C:47]([C:48]([OH:50])=[O:49])=[CH:46][CH:45]=[C:44]([C:53]([F:54])([F:55])[F:56])[N:43]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]2[NH:22][N:21]=[N:20][N:19]=2)=[CH:8][CH:7]=1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 521998p-Toluenesulfonic acid monohydrateHCID 19792029HCID 19792029, compound

Product 1

HCID 178457029HCID 178457029, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Ethyl 6-trifluoromethylpyridin-2-one-3-carboxylate, prepared by the method described in Helv. Chim. Acta. 71, 596 (1988), is chlorinated with phosphorus oxychloride to give the 2-chloro compound. Treatment of ethyl 2-chloro-6-trifluoromethylpyridine-3-carboxylate with N-triphenylmethyl-5-[2-(4'-propylaminomethyl-biphenyl)]tetrazole, prepared as described in Example 72B, in tetrahydrofuran containing triethylamine affords the tertiary amine. Treatment of ethyl 2-{N-propyl-N-[(2'-[N-triphenylmethyl-1H-tetrazol-5-yl]biphenyl-4-yl)methyl]amino}-6-trifluoromethyl-pyridine-3-carboxylate with p-toluenesulfonic acid monohydrate in methanol to detritylate followed by sodium hydroxide in methanol hydrolysis gives the title compound.

Sources & evidence

ORD record
ord-5df91f4412ba475c95388e818eacf4bf
Source dataset
uspto-grants-1993_10
Patent number
US05250548

Reaction notes

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