Sodium Iodide → 2-ethylbutanoic acid 5-{(4-{amino[2,2-dimethylpropoxycarbonylimino]methyl}phenylamino)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxymethyl ester

HRID 2089633Notes

Reaction equation

HRID 2089633 reaction equation
[CH3:1][C:2]([CH3:46])([CH3:45])[CH2:3][O:4][C:5](=[O:44])[N:6]=[C:7]([NH2:43])[C:8]1[CH:13]=[CH:12][C:11]([NH:14][CH:15]([C:29]2[N:33]=[C:32]([O:34][CH2:35]Cl)[N:31]([C:37]3[N:42]=[CH:41][CH:40]=[CH:39][N:38]=3)[N:30]=2)[C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:24][CH2:25][CH2:26][OH:27])[C:17]=2[F:28])=[CH:10][CH:9]=1.C(=O)([O-])O.[K+].[CH2:52]([CH:54]([CH2:58][CH3:59])[C:55]([OH:57])=[O:56])[CH3:53].[I-].[Na+].[Cl-].[NH4+]>CN(C=O)C>[NH2:43][C:7](=[N:6][C:5]([O:4][CH2:3][C:2]([CH3:46])([CH3:45])[CH3:1])=[O:44])[C:8]1[CH:13]=[CH:12][C:11]([NH:14][CH:15]([C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:24][CH2:25][CH2:26][OH:27])[C:17]=2[F:28])[C:29]2[N:33]=[C:32]([O:34][CH2:35][O:57][C:55](=[O:56])[CH:54]([CH2:58][CH3:59])[CH2:52][CH3:53])[N:31]([C:37]3[N:42]=[CH:41][CH:40]=[CH:39][N:38]=3)[N:30]=2)=[CH:10][CH:9]=1

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 69152-Ethylbutyric acidHCID 25517Ammonium ChlorideHCID 516893Potassium BicarbonateHCID 67470504[1-amino-1-[4-({(5-chloromethoxy-1-pyrimidin-2-yl-1H-[1,2,4]triazol-3-yl)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}amino)phenyl]methylidene]carbamic acid 2,2-dimethylpropyl ester

Product 1

HCID 674705332-ethylbutanoic acid 5-{(4-{amino[2,2-dimethylpropoxycarbonylimino]methyl}phenylamino)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxymethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

To a mixture of [1-amino-1-[4-({(5-chloromethoxy-1-pyrimidin-2-yl-1H-[1,2,4]triazol-3-yl)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}amino)phenyl]methylidene]carbamic acid 2,2-dimethylpropyl ester (Example 2b, 100 mg), potassium hydrogen carbonate (109 mg), and DMF (13.3 mL), 2-ethylbutanoic acid (88.3 mg) and sodium iodide (117 mg) were added, and the resulting mixture was stirred at 45° C. overnight and then cooled to room temperature. To the reaction mixture, ice and saturated aqueous ammonium chloride solution were added, and the resulting mixture was extracted with a mixture of THF and ethyl acetate. The organic layer was washed with saturated aqueous ammonium chloride solution and dried over anhydrous magnesium sulfate.

Workup

  1. additionwere added
  2. temperaturecooled to room temperature
  3. extractionthe resulting mixture was extracted with a mixture of THF and ethyl acetate
  4. washThe organic layer was washed with saturated aqueous ammonium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-8fc14fadca3a4714a8da516d246b9a1b
Source dataset
uspto-grants-2013_05
Patent number
US08436009B2

Reaction notes

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