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Sodium Hydroxide → 4-(5-{5-Methyl-3-[3-(methylsulfonyl)propyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]-2,3-dihydro-1H-imidazol-4-yl}-1H-pyrazol-1-yl)benzonitrile

HRID 1480021
Notes
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Reaction equation

HRID 1480021 reaction equation
C([O:3][C:4]1[N:5]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=2)[C:6]([CH3:22])=[C:7]([C:9]2[N:13]([C:14]3[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=3)[N:12]=[CH:11][CH:10]=2)[N:8]=1)C.Br[CH2:34][CH2:35][CH2:36][S:37]([CH3:40])(=[O:39])=[O:38].[OH-].[Na+]>C(#N)C.O>[CH3:22][C:6]1[N:5]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:31])([F:32])[F:30])[CH:24]=2)[C:4](=[O:3])[N:8]([CH2:34][CH2:35][CH2:36][S:37]([CH3:40])(=[O:39])=[O:38])[C:7]=1[C:9]1[N:13]([C:14]2[CH:15]=[CH:16][C:17]([C:18]#[N:19])=[CH:20][CH:21]=2)[N:12]=[CH:11][CH:10]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 518920821-Bromo-3-methanesulfonylpropaneHCID 1213937624-(5-{2-Ethoxy-5-methyl-1-[3-(trifluoromethyl)phenyl]-1H-imidazol-4-yl}-1H-pyrazol-1-yl)benzonitrile2×

Product 1

HCID 1213936904-(5-{5-Methyl-3-[3-(methylsulfonyl)propyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]-2,3-dihydro-1H-imidazol-4-yl}-1H-pyrazol-1-yl)benzonitrileYield 12.6%

Reagents, catalysts & solvents

2
HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
120 °C

Procedure

A mixture of 4-(5-{2-ethoxy-5-methyl-1-[3-(trifluoromethyl)phenyl]-1H-imidazol-4-yl}-1H-pyrazol-1-yl)benzonitrile (intermediate 5) (66 mg, 0.15 mmol) and 1-bromo-3-methanesulfonyl propane (201 mg, 1.0 mmol) in acetonitrile (0.20 mL) was heated at 120° C. for 6 h. The mix was cooled to RT and diluted with acetonitrile (2 mL) and water (1 mL) then treated with 1M sodium hydroxide (0.20 ml). The mixture was heated at 50° C. for 2 h. The cold mixture was diluted with water (10 mL) and extracted with EtOAc (2×10 mL). The combined organic phase was dried (sodium sulfate) and concentrated in vacuo. The residue was purified by MDAP to afford the title compound (10 mg).

Workup

  1. temperatureThe mix was cooled to RT
  2. temperatureThe mixture was heated at 50° C. for 2 h
  3. extractionextracted with EtOAc (2×10 mL)
  4. dry with materialThe combined organic phase was dried (sodium sulfate)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by MDAP

Sources & evidence

ORD record
ord-2ca51a3eea9a414196a642b265379c61
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09409870B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes