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 1480021Notes

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

Participants

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

temperatureThe mix was cooled to RT
temperatureThe mixture was heated at 50° C. for 2 h
extractionextracted with EtOAc (2×10 mL)
dry with materialThe combined organic phase was dried (sodium sulfate)
concentrationconcentrated in vacuo
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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