Ethyl Acetate → 1-(2-((4-Cyanobenzyl)amino)pyrimidin-4-yl)-3-ethyl-2-oxopyrrolidine-3-carbonitrile

HRID 714808Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:12][CH2:11][C:10]([CH2:15][CH3:16])([C:13]#[N:14])[C:9]2=[O:17])[CH:5]=[CH:4][N:3]=1.Cl.[NH2:19][CH2:20][C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=1.C(N(C(C)C)CC)(C)C.C(OCC)(=O)C>CN1CCCC1=O.O>[C:20]([C:21]1[CH:28]=[CH:27][C:24]([CH2:25][NH:26][C:2]2[N:7]=[C:6]([N:8]3[CH2:12][CH2:11][C:10]([CH2:15][CH3:16])([C:13]#[N:14])[C:9]3=[O:17])[CH:5]=[CH:4][N:3]=2)=[CH:23][CH:22]=1)#[N:19]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-(2-chloropyrimidin-4-yl)-3-ethyl-2-oxopyrrolidine-3-carbonitrile (20 mg) obtained in Step A of Example 2 and 4-(aminomethyl)benzonitrile hydrochloride (27 mg) in N-methylpyrrolidone (2 mL) was added diisopropylethylamine (0.028 mL), and the mixture was stirred at 60° C. for 3 hr. To the reaction mixture were added ethyl acetate (3 mL) and water (1 mL), and the mixture was stirred for 5 min. The organic layer was filtered through Top-Phase Separation Filter Tube, and the solvent was evaporated at 60° C. The residue was purified by HPLC (C18, mobile phase: acetonitrile/10 mM aqueous ammonium hydrogen carbonate solution), and dried at 60° C. to give the title compound.

Workup

stirringthe mixture was stirred for 5 min
filtrationThe organic layer was filtered through Top-Phase Separation
filtrationFilter Tube
customthe solvent was evaporated at 60° C
customThe residue was purified by HPLC (C18, mobile phase: acetonitrile/10 mM aqueous ammonium hydrogen carbonate solution)
customdried at 60° C.

Sources & evidence

ORD record: ord-e6112ecfbebd40688594df77fb7b7534
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187453B2

Reaction notes

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