Diisopropylethylamine → Ethyl {4-[((2-methoxyethyl){6-[4-(trifluoromethyl) phenyl]pyrazin-2-yl}amino)methyl]-2-methylphenoxy}acetate

HRID 1269638Notes

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.[CH3:27][O:28][CH2:29][CH2:30][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>O>[CH3:27][O:28][CH2:29][CH2:30][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

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-bromo-6-[4-(trifluoromethyl)phenyl]pyrazine (0.5 g, 1.65 mmol), N,N-diisopropylethylamine (0.29 mL, 1.65 mmol) and ethyl (4-{[(2-methoxyethyl)amino]methyl}-2-methylphenoxy)acetate (0.7 g, 2.47 mmol) was heated at 100° C. in a sealed reactivial for 20 h. The reaction mixture was then allowed to come to room temperature, and the residue was diluted with water (40 mL) and extracted CH2Cl2 (2×40 mL). The organic extract was 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 (0.16 g).

Workup

customto come to room temperature
extractionextracted CH2Cl2 (2×40 mL)
extractionThe organic extract
concentrationconcentrated in vacuo
customPurification by Biotage™ chromatography (Silica, 90 g)
washeluting 1:19–1:4 EtOAc

Sources & evidence

ORD record: ord-618aea29db5148b982dbdabc333387f2
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199239B2

Reaction notes

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