Diisopropylethylamine → Methyl-3-[3-({1-[2-(benzyloxy)phenyl]-1-methylethyl}amino)-2-oxopyrazin-1(2H)-yl]-4-chlorobenzoate

HRID 2070851Notes

Reaction equation

Br[C:2]1[C:3](=[O:19])[N:4]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=2[Cl:18])[C:11]([O:13][CH3:14])=[O:12])[CH:5]=[CH:6][N:7]=1.C(N(C(C)C)C(C)C)C.[CH2:29]([O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[C:43]([NH2:46])([CH3:45])[CH3:44])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1(C)C=CC=CC=1.O>[CH3:14][O:13][C:11](=[O:12])[C:10]1[CH:15]=[CH:16][C:17]([Cl:18])=[C:8]([N:4]2[CH:5]=[CH:6][N:7]=[C:2]([NH:46][C:43]([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=3[O:36][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([CH3:45])[CH3:44])[C:3]2=[O:19])[CH:9]=1

Participants

Conditions

Temperature: 125 °C

Procedure

A solution of methyl 3-(3-bromo-2-oxopyrazin-1(2H)-yl)-4-chlorobenzoate (Example 330e, 3 g) dissolved in toluene (15 mL) was treated with N-ethyldiisopropylamine (2.99 mL) and 2-(2-(benzyloxy)phenyl)propan-2-amine (Example 198d 2.107 g) under nitrogen. The resulting mixture was stirred at 125° C. for 8 h in a sealed tube. The reaction mixture was diluted with water (150 mL), and extracted with ethyl acetate (250 mL). The organic was dried (MgSO4), filtered and evaporated to afford crude product. Purification (SiO2 chromatography eluting with 50% diethyl ether in isohexane) gave the subtitle compound (2.230 g).

Workup

extractionextracted with ethyl acetate (250 mL)
dry with materialThe organic was dried (MgSO4)
filtrationfiltered
customevaporated
customto afford crude product
customPurification (SiO2 chromatography eluting with 50% diethyl ether in isohexane)

Sources & evidence

ORD record: ord-d3e06e1817b2485287ea751f3287b86e
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299246B2

Reaction notes

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