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

HRID 337064Notes

Reaction equation

Br[C:2]1[C:3](=[O:22])[N:4]([C:9]2[CH:10]=[C:11]([CH:17]=[C:18]([F:21])[C:19]=2[CH3:20])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[C:6]([Br:8])[N:7]=1.[CH3:23][C:24]([CH3:40])([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[NH2:25].C(N(C(C)C)C(C)C)C>O1CCOCC1.O>[Br:8][C:6]1[N:7]=[C:2]([NH:25][C:24]([CH3:40])([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH3:23])[C:3](=[O:22])[N:4]([C:9]2[CH:10]=[C:11]([CH:17]=[C:18]([F:21])[C:19]=2[CH3:20])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

3-(3,5-Dibromo-2-oxo-1(2H)-pyrazinyl)-5-fluoro-4-methyl-benzoic acid, ethyl ester (Example 169d, 1.137 g, 2.62 mmol) was dissolved in dioxane (10 mL). α,α-Dimethyl-2-(phenylmethoxy)-benzenemethanamine (Example 134a, 0.63 g) and N-ethyldiisopropylamine (0.67 mL, 3.93 mmol) were added under nitrogen and the resulting solution was stirred at 100° C. for 10 h. The reaction mixture was diluted with water (50 mL), and extracted with ethyl acetate (100 mL×2). The combined organics were dried (MgSO4), filtered and evaporated to afford the crude product. This was purified by (SiO2 chromatography eluting with dichloromethane) to afford the subtitle product (1.55 g).

Workup

extractionextracted with ethyl acetate (100 mL×2)
dry with materialThe combined organics were dried (MgSO4)
filtrationfiltered
customevaporated
customto afford the crude product
customThis was purified by (SiO2 chromatography eluting with dichloromethane)

Sources & evidence

ORD record: ord-03460974edb24919b7af7f39dc471372
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889692B2

Reaction notes

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