Diisopropylethylamine → HCID 86626402, compound

HRID 388117Notes

Reaction equation

HRID 388117 reaction equation
[Br:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:12][CH:13]3[CH2:17][CH2:16][C:15](=[O:18])[NH:14]3)C(=O)[NH:10][C:5]2=[N:4][CH:3]=1.BrC1C(N)=NC=C(Br)N=1.Cl.NCC1NC(=O)CC1.C(N(C(C)C)CC)(C)C>CS(C)=O>[NH2:10][C:5]1[C:6]([NH:8][CH2:12][CH:13]2[NH:14][C:15](=[O:18])[CH2:16][CH2:17]2)=[N:7][C:2]([Br:1])=[CH:3][N:4]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 6200042-Amino-3,5-dibromopyrazineHCID 141431905-(Aminomethyl)pyrrolidin-2-one--hydrogen chloride (1/1)HCID 86626403HCID 86626403, compound

Product 1

HCID 86626402HCID 86626402, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

6-Bromo-1-((5-oxopyrrolidin-2-yl)methyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one. 3,5-Dibromopyrazin-2-amine (253 mg, 1 mmol), 5-(aminomethyl)pyrrolidin-2-one hydrochloride (150 mg, 1 mmol), diisopropylethylamine (0.5 mL), and dimethylsulfoxide (2 mL) were heated in a Biotage Emrys Optimizer microwave reactor at 150° C. for 2 h to afford crude 5-((3-amino-6-bromopyrazin-2-ylamino)methyl)pyrrolidin-2-one. MS (ESI) m/z 286.0 [M]+, 288.0 [M+2] +. 1,1′-Carbonyldiimidazole (243 mg, 1.5 mmol) was added to the reaction mixture and the solution was heated again in a Biotage Emrys Optimizer microwave reactor at 150° C. for 10 min. The product was purified by reverse-phase semi-preparatory HPLC (10-70% acetonitrile+0.1% TFA in H2O+0.1% TFA, over 30 min). The product fractions were concentrated and then triturated with ether to give a white solid. MS (ESI) m/z 312.0 [M]+, 314.0 [M+2]+.

Sources & evidence

ORD record
ord-8fd90e1a15374da39555dabdb71aa0ab
Source dataset
uspto-grants-2013_02
Patent number
US08372976B2

Reaction notes

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