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Ethyl Acetate → 4-(2-{(3-Cyano-5-trifluoromethyl-benzyl)-[2-(cyclopropylmethyl-propyl-amino)-5-trifluoromethyl-benzyl]-amino}-pyrimidin-5-yloxy)-butyric acid

HRID 604090
Notes
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Reaction equation

HRID 604090 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:42]=[C:43]([C:45]([F:48])([F:47])[F:46])[CH:44]=1)[CH2:6][N:7]([CH2:23][C:24]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][C:25]=1[N:34]([CH2:38][CH:39]1[CH2:41][CH2:40]1)[CH2:35][CH2:36][CH3:37])[C:8]1[N:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][C:18]([O:20]CC)=[O:19])=[CH:10][N:9]=1)#[N:2].[OH-].[Na+].C(OCC)(=O)C>O1CCCC1>[C:1]([C:3]1[CH:4]=[C:5]([CH:42]=[C:43]([C:45]([F:48])([F:46])[F:47])[CH:44]=1)[CH2:6][N:7]([CH2:23][C:24]1[CH:29]=[C:28]([C:30]([F:32])([F:33])[F:31])[CH:27]=[CH:26][C:25]=1[N:34]([CH2:38][CH:39]1[CH2:40][CH2:41]1)[CH2:35][CH2:36][CH3:37])[C:8]1[N:9]=[CH:10][C:11]([O:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:12][N:13]=1)#[N:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium Hydroxide2×HCID 86626842Ethyl 4-(2-{(3-cyano-5-trifluoromethyl-benzyl)-[2-(cyclopropylmethyl-propyl-amino)-5-trifluoromethyl-benzyl]-amino}-pyrimidin-5-yloxy)-butyrate

Product 1

HCID 866268444-(2-{(3-Cyano-5-trifluoromethyl-benzyl)-[2-(cyclopropylmethyl-propyl-amino)-5-trifluoromethyl-benzyl]-amino}-pyrimidin-5-yloxy)-butyric acidYield 82.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

Ethyl 4-(2-{(3-cyano-5-trifluoromethyl-benzyl)-[2-(cyclopropylmethyl-propyl-amino)-5-trifluoromethyl-benzyl]-amino}-pyrimidin-5-yloxy)-butyrate (240 mg) is dissolved in tetrahydrofuran (2.6 ml), and thereto is added 1N-aqueous sodium hydroxide solution (2.6 ml) and the mixture is stirred at 40° C. for additional 30 minutes and warmed to 50° C. and stirred for 3 hours. Thereto is added a 2N-aqueous sodium hydroxide solution (650 μl) and the mixture is stirred at 60° C. for 20 minutes. The reaction solution is cooled to room temperature and thereto are added ethyl acetate and a 1N-hydrochloric acid, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over sodium sulfate and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (chloroform:methanol=19:1) to give 4-(2-{(3-cyano-5-trifluoromethyl-benzyl)-[2-(cyclopropylmethyl-propyl-amino)-5-trifluoromethyl-benzyl]-amino}-pyrimidin-5-yloxy)-butyric acid (189 mg). MS (m/z): 650 [M+H]+

Workup

  1. temperaturewarmed to 50° C.
  2. stirringstirred for 3 hours
  3. stirringthe mixture is stirred at 60° C. for 20 minutes
  4. temperatureThe reaction solution is cooled to room temperature
  5. customa 1N-hydrochloric acid, and the mixture is separated
  6. washthe organic layer is washed with a saturated brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue is purified by silica gel column chromatography (chloroform:methanol=19:1)

Sources & evidence

ORD record
ord-676a6e5882c24fe4859e384de4561b9f
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07906517B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes