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

HRID 337171Notes

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-06874e76056f410ca7cd96dbfa3c262f
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889692B2

Reaction notes

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