Toluene → HCID 58181279, compound

HRID 1765997Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[Cl:20][C:21]1[C:26]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:24]=[C:23](Cl)[N:22]=1.C1(C)C=CC=CC=1>CS(C)=O.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:23]2[CH:24]=[CH:25][C:26]([C:27]([F:29])([F:30])[F:28])=[C:21]([Cl:20])[N:22]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of tert-butyl-1-piperazine carboxylate (27.0 g, 145 mmol) and K2CO3 (40.0 g, 290 mmol) in DMSO (200 mL) were 2,6-dichloro-3-trifluoromethylpyridine (29.1 g, 135 mmol) and toluene (50 mL) added. The thick slurry was stirred at 80° C. for two hours, followed by addition of toluene (0.5 L) and water (1 L). The phases were separated and the organic phase was washed twice with water. The solvent from the dried (MgSO4) organic phase was evaporated at reduced pressure. The solid residue was recrystallized from EtOAc/heptane to give white crystals (37 g). The filtrate from the recrystallization was concentrated and the residue chromatographed on a column of silica with hexane/EtOAc (90:10) to give further 6.0 g of product (total yield 85%). Purity 99% (HPLC); mp 125° C. Anal. (C15H19ClF3N3O2) C, H, N.

Workup

additionadded
customThe phases were separated
washthe organic phase was washed twice with water
dry with materialThe solvent from the dried (MgSO4) organic phase
customwas evaporated at reduced pressure
customThe solid residue was recrystallized from EtOAc/heptane

Sources & evidence

ORD record: ord-e9889d16f0a948e79975aa609a51792c
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07229997B2

Reaction notes

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