Lithium iodide → HCID 59613532, compound
Reaction equation
[C:1]([C:3]1[N:4]=[CH:5][C:6]([NH:9][C:10]2[CH:19]=[C:18]([NH:20][CH:21]3[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]3)[C:13]([C:14]([O:16]C)=[O:15])=[CH:12][N:11]=2)=[N:7][CH:8]=1)#[N:2].[I-].[Li+]>N1C=CC=CC=1>[C:1]([C:3]1[N:4]=[CH:5][C:6]([NH:9][C:10]2[CH:19]=[C:18]([NH:20][CH:21]3[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]3)[C:13]([C:14]([OH:16])=[O:15])=[CH:12][N:11]=2)=[N:7][CH:8]=1)#[N:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Methyl 6-(5-cyanopyrazin-2-ylamino)-4-(1-methylpiperidin-4-ylamino)nicotinate (Synthesis 66) (50 mg, 0.136 mmol) and lithium iodide (36 mg, 2 eq.) in dry pyridine (1.4 mL) were heated at 150° C. in a sealed Biotage microwave vial for 2.5 hr. The volatiles were removed in vacuo and the crude mixture was partitioned between EtOAc and 1M aqueous NaHCO3. The aqueous layer was retained, washed with fresh EtOAc and then carefully neutralised with 1M HCl. The volatiles were then removed and a portion of the residue was purified by HPLC to give the title compound as a yellow powder (5 mg, 10%).