Diisopropylethylamine → methyl 5-[3-({1-[2-(benzyloxy)phenyl]cyclopropyl}amino)-5-bromo-2-oxopyrazin-1(2H)-yl]-2-fluoro-4-methylbenzoate

HRID 337141Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 1-(2-(benzyloxy)phenyl)cyclopropanamine (1.026 g) in dioxane (10 mL) was treated with methyl 5-(3,5-dibromo-2-oxopyrazin-1(2H)-yl)-2-fluoro-4-methylbenzoate (Example 318d, 1.500 g) and Hunig's Base (0.936 mL) under nitrogen. The resulting solution was stirred at 100° C. for 16 h. The cooled mixture was diluted with 2 M HCl and extracted with diethyl ether. The combined organics were dried (MgSO4) and evaporated to afford the subtitle compound (2.310 g) as a foam.

Workup

extractionextracted with diethyl ether
dry with materialThe combined organics were dried (MgSO4)
customevaporated

Sources & evidence

ORD record: ord-459717f7cdc04a2db238447b3f72aae5
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889692B2

Reaction notes

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