Diisopropylethylamine → 3-[5-Bromo-3-[[1-methyl-1-[2-(phenylmethoxy)phenyl]ethyl]amino]-2-oxo-1(2H)-pyrazinyl]-4-methyl-benzoic acid methyl ester

HRID 337074Notes

Reaction equation

[CH3:1][C:2]([CH3:18])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[NH2:3].Br[C:20]1[C:21](=[O:38])[N:22]([C:27]2[CH:28]=[C:29]([CH:34]=[CH:35][C:36]=2[CH3:37])[C:30]([O:32][CH3:33])=[O:31])[CH:23]=[C:24]([Br:26])[N:25]=1.C(N(C(C)C)C(C)C)C>O1CCOCC1.O>[CH3:33][O:32][C:30](=[O:31])[C:29]1[CH:34]=[CH:35][C:36]([CH3:37])=[C:27]([N:22]2[CH:23]=[C:24]([Br:26])[N:25]=[C:20]([NH:3][C:2]([CH3:18])([C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[O:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH3:1])[C:21]2=[O:38])[CH:28]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of α,α-dimethyl-2-(phenylmethoxy)-benzenemethanamine (Example 198d, 1.5 g) dissolved in dioxane (52.2 mL) was treated with methyl 3-(3,5-dibromo-2-oxopyrazin-1(2H)-yl)-4-methylbenzoate (Example 1b, 2.499 g) and N-ethyldiisopropylamine (1.083 mL) under nitrogen. The resulting solution was stirred at 100° C. for 10 h. After cooling to room temperature, the reaction mixture was diluted with water (50 mL), and extracted with ethyl acetate (100 mL×2). The organic was dried (MgSO4), filtered and evaporated. The crude product was trituated with 50% diethyl ether in iso-hexane for 3 h. The solid was filtered off to afford the subtitle compound (2.405 g).

Workup

temperatureAfter cooling to room temperature
extractionextracted with ethyl acetate (100 mL×2)
dry with materialThe organic was dried (MgSO4)
filtrationfiltered
customevaporated
waitThe crude product was trituated with 50% diethyl ether in iso-hexane for 3 h
filtrationThe solid was filtered off

Sources & evidence

ORD record: ord-39545e284fbb464f92e20588277ec962
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889692B2

Reaction notes

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