Lithium iodide → HCID 59613532, compound

HRID 384670Notes

Reaction equation

HRID 384670 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

HCID 66321Lithium iodideHCID 42610235HCID 42610235, compound

Product 1

HCID 59613532HCID 59613532, compoundYield 10.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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%).

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe crude mixture was partitioned between EtOAc and 1M aqueous NaHCO3
  3. washwashed with fresh EtOAc
  4. customThe volatiles were then removed
  5. customa portion of the residue was purified by HPLC

Sources & evidence

ORD record
ord-57269b561f2042a9a51adf905833997c
Source dataset
uspto-grants-2013_02
Patent number
US08367658B2

Reaction notes

Loading…