Hydrochloric Acid → (3-{6-[2-(2,4-Dichloro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-benzoylamino)-acetic acid

HRID 216190Notes

Reaction equation

HRID 216190 reaction equation
C([O:3][C:4](=[O:34])[CH2:5][NH:6][C:7](=[O:33])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:19]=[C:18]([NH:20][CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=3[Cl:30])[N:17]=[C:16]([O:31][CH3:32])[N:15]=2)[CH:9]=1)C.[OH-].[Li+].Cl>C1COCC1.CO.O>[Cl:30][C:24]1[CH:25]=[C:26]([Cl:29])[CH:27]=[CH:28][C:23]=1[CH2:22][CH2:21][NH:20][C:18]1[N:17]=[C:16]([O:31][CH3:32])[N:15]=[C:14]([C:10]2[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=2)[C:7]([NH:6][CH2:5][C:4]([OH:34])=[O:3])=[O:33])[CH:19]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 11706060(3-{6-[2-(2,4-Dichloro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-benzoylamino)-acetic acid ethyl ester

Product 1

HCID 11518514(3-{6-[2-(2,4-Dichloro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-benzoylamino)-acetic acidYield 43%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (3-{6-[2-(2,4-dichloro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-benzoylamino)-acetic acid ethyl ester [120 mg, 0.24 mmol, Example 58], lithium hydroxide (20 mg, 0.48 mmol) in THF (1 mL), MeOH (1 mL) and water (1 mL) is stirred for 20 hours at ambient temperature. The mixture is acidified to pH 1 with 10% hydrochloric acid and extracted three times with EtOAc (25 mL). The organic extracts are combined and dried over magnesium sulfate, filtered and concentrated by rotary evaporator to provide (3-{6-[2-(2,4-dichloro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-benzoylamino)-acetic acid [49 mg, 43%, Example 59]. LCMS: RT=2.77 minutes, MS: 475 (M+H). IC50=0.8 nM

Workup

  1. extractionextracted three times with EtOAc (25 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated by rotary evaporator

Sources & evidence

ORD record
ord-b8ca568ccafe43de9c3a932336381a89
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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