Sodium Hydroxide → HCID 21948898, compound

HRID 2055014Notes

Reaction equation

HRID 2055014 reaction equation
[H-].[Na+].C([NH:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][C:11]([CH3:17])=[N:12]2)(=O)C.[F:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=1[C:26]1([CH2:29][C:30]([C:44]([F:47])([F:46])[F:45])([OH:43])[CH2:31]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:28][CH2:27]1.[OH-].[Na+]>CCCCCC.C(OCC)(=O)C>[F:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=1[C:26]1([CH2:29][C:30]([C:44]([F:47])([F:45])[F:46])([OH:43])[CH:31]([NH:6][C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[CH:9]=[CH:10][C:11]([CH3:17])=[N:12]3)[NH:6][C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[CH:9]=[CH:10][C:11]([CH3:17])=[N:12]3)[CH2:28][CH2:27]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 64612065-acetylamino-2-methyl-quinolineHCID 21948907HCID 21948907, compound

Product 1

HCID 21948898HCID 21948898, compoundYield 18.4%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Analogously to Example 76, 60 mg (1.46 mmol) of NaH (60%) and 244 mg (1.23 mmol) of 5-acetylamino-2-methyl-quinoline are reacted with 365 mg (0.81 mmol) of toluene-4-sulfonic acid-3-[1-(2,5-difluorophenyl)-cycloprop-1-yl]-2-(trifluoromethyl)-2-hydroxy-propyl ester. The crude product is treated analogously to Example 76 with 1 M sodium hydroxide solution. After chromatography on silica gel with hexane-ethyl acetate (30-50%), 67 mg of product is obtained.

Sources & evidence

ORD record
ord-941e16a374c24b03a6509adf59883b5c
Source dataset
uspto-grants-2008_02
Patent number
US07329753B2

Reaction notes

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