Potassium Carbonate → HCID 59370370, compound

HRID 448944Notes

Reaction equation

HRID 448944 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]([CH3:21])[C:9]2[CH:20]=[CH:19][CH:18]=[CH:17][C:10]=2[O:11][CH2:12][CH2:13]C(O)=O)=[O:7])=[CH:4][C:3]=1[C:24]1[CH:25]=[N:26][C:27]([C:32]([F:35])([F:34])[F:33])=[CH:28][C:29]=1[C:30]#[N:31].[CH3:36][S:37]([NH2:40])(=[O:39])=[O:38].[C:41]([O-:44])([O-])=O.[K+].[K+].C1(P([N:61]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.OS([O-])(=O)=O.[Na+]>O1CCOCC1.O>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]([C:9]2[CH:20]=[CH:19][CH:18]=[CH:17][C:10]=2[O:11][CH2:12][CH2:13][NH:61][C:41]([NH:40][S:37]([CH3:36])(=[O:39])=[O:38])=[O:44])[CH3:21])=[O:7])=[CH:4][C:3]=1[C:24]1[CH:25]=[N:26][C:27]([C:32]([F:35])([F:34])[F:33])=[CH:28][C:29]=1[C:30]#[N:31]

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 72879MethanesulfonamideHCID 199401P,P-Diphenylphosphinic azideHCID 516919Sodium BisulfateHCID 251587413-(2-{[4-Chloro-3-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenoxy)-propionic acid

Product 1

HCID 59370370HCID 59370370, compoundYield 6.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of 3-(2-{[4-chloro-3-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenoxy)-propionic acid 11-4 (272.9 mg, 0.54 mmol), CH3SO2NH2 (51.5 mg, 0.54 mmol) and K2CO3 (224.4 mg, 1.63 mmol) in dioxane (4.0 mL), was added diphenylphosphoryl azide (141 μL, 0.65 mmol). The mixture was heated at 85° C. for 3 hrs, diluted with water, acidified to pH 3 by NaHSO4 aqueous solution, then extracted with ethyl acetate. The organic solution was then dried, concentrated and purified by prep. TLC plate eluting with 4% MeOH in dichloromethane to afford 4-chloro-3-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-N-{2-[2-(3-methylsulfonyl-ureido)-ethoxy]-phenyl}-N-methyl-benzamide 41-1 (20.5 mg). MS [M+H]+596.3; tR=7.29 min (method 2).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic solution was then dried
  3. concentrationconcentrated
  4. custompurified by prep
  5. washTLC plate eluting with 4% MeOH in dichloromethane

Sources & evidence

ORD record
ord-1368a0a558384c66a75c802f4a580582
Source dataset
uspto-grants-2013_07
Patent number
US08481738B2

Reaction notes

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