Hydrochloric Acid → HCID 67426063, compound

HRID 505966Notes

Reaction equation

HRID 505966 reaction equation
[OH-].[Li+].C([O:5][C:6](=[O:31])[C:7]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[C:10]([CH2:23][CH2:24][C:25]2[CH:26]=[N:27][CH:28]=[N:29][CH:30]=2)=[N:9][CH:8]=1)C.COC(=O)C1C=C(C2C=CC(C(F)(F)F)=CC=2)C(CCC2C=NC=NC=2)=NC=1.Cl.O1CCOCC1>O1CCCC1.CO>[N:29]1[CH:30]=[C:25]([CH2:24][CH2:23][C:10]2[C:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:20])[F:21])=[CH:15][CH:14]=3)=[CH:12][C:7]([C:6]([OH:31])=[O:5])=[CH:8][N:9]=2)[CH:26]=[N:27][CH:28]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 312751,4-DioxaneHCID 67426677HCID 67426677, compoundHCID 67426708HCID 67426708, compound

Product 1

HCID 67426063HCID 67426063, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Aqueous 1M lithium hydroxide solution (2.25 ml, 2.25 mmol) was added to a solution of 6-(2-pyrimidin-5-yl-ethyl)-5-(4-trifluoromethyl-phenyl)-nicotinic acid ethyl ester and 6-(2-pyrimidin-5-yl-ethyl)-5-(4-trifluoromethyl-phenyl)-nicotinic acid methyl ester (46:54, 196 mg, 0.49 mmol) in tetrahydrofuran and methanol (6:1, 7 ml). The reaction mixture was stirred for 20 hours at room temperature then concentrated in vacuo. The residue was treated with 4M HCl in dioxane (0.56 ml, 2.25 mmol) and concentrated in vacuo to give crude 6-(2-pyrimidin-5-yl-ethyl)-5-(4-trifluoromethyl-phenyl)-nicotinic acid. This material was used in the subsequent amide coupling step without further purification. LC at 215 nm; Rt 1.72: 89%, m/z (ES+): 374 (M+H).

Workup

  1. concentrationthen concentrated in vacuo
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-493406ab2b764550818ecaf350c3f791
Source dataset
uspto-grants-2010_08
Patent number
US07781593B2

Reaction notes

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