Diisopropylethylamine → HCID 58622852, compound

HRID 1269636Notes

Reaction equation

Br[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[N:3]=1.C(N(CC)C(C)C)(C)C.[CH2:27]([NH:31][CH2:32][C:33]1[CH:45]=[CH:44][C:36]([O:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])=[C:35]([CH3:46])[CH:34]=1)[CH2:28][CH2:29][CH3:30]>C(Cl)Cl>[CH2:27]([N:31]([CH2:32][C:33]1[CH:45]=[CH:44][C:36]([O:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])=[C:35]([CH3:46])[CH:34]=1)[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[N:3]=1)[CH2:28][CH2:29][CH3:30]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-bromo-6-[4-(trifluoromethyl)phenyl]pyrazine (0.5 g, 1.6 mmol), N,N-diisopropylethylamine (0.29 mL, 1.6 mmol) and ethyl {4-[(butylamino)methyl]-2-methylphenoxy}acetate (0.5 g, 1.8 mmol) was heated at 100° C. in a sealed reactivial for 18 h. The reaction mixture was then allowed to come to room temperature, and the residue dissolved in CH2Cl2 (130 mL), the organic extract was washed water (30 mL) passed through a hydrophobic frit and concentrated in vacuo. Purification by Biotage™ chromatography (Silica, 90 g) eluting 1:19–1:4 EtOAc:cyclohexane afforded the title compound as a pale yellow oil (0.15 g).

Workup

customto come to room temperature
extractionthe organic extract
washwas washed water (30 mL)
concentrationconcentrated in vacuo
customPurification by Biotage™ chromatography (Silica, 90 g)
washeluting 1:19–1:4 EtOAc

Sources & evidence

ORD record: ord-8ba4f5dc640f4ac4aea3c1f2ab7f2249
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199239B2

Reaction notes

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