Lithium Hydroxide → 2-(1-Methyl-6-oxopyrido[2,3-e]pyrrolo[1,2-a]pyrazin-5(6H)-yl)acetic acid

HRID 526043Notes

Reaction equation

HRID 526043 reaction equation
[CH3:1][C:2]1[C:11]2[N:10]3[CH:12]=[CH:13][CH:14]=[C:9]3[C:8](=[O:15])[N:7]([CH2:16][C:17]([O:19]C)=[O:18])[C:6]=2[N:5]=[CH:4][CH:3]=1.[Li+].[OH-]>CO.O.C1COCC1>[CH3:1][C:2]1[C:11]2[N:10]3[CH:12]=[CH:13][CH:14]=[C:9]3[C:8](=[O:15])[N:7]([CH2:16][C:17]([OH:19])=[O:18])[C:6]=2[N:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 89451658Methyl 2-(1-methyl-6-oxopyrido[2,3-e]pyrrolo[1,2-a]pyrazin-5(6H)-yl)acetate

Product 1

HCID 894516542-(1-Methyl-6-oxopyrido[2,3-e]pyrrolo[1,2-a]pyrazin-5(6H)-yl)acetic acidYield 73%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Methyl 2-(1-methyl-6-oxopyrido[2,3-e]pyrrolo[1,2-a]pyrazin-5(6H)-yl)acetate (517 mg, 1.91 mmol) was dissolved in 20 mL of MeOH/H2O/THF (1:1:4). LiOH (68.5 mg, 2.86 mmol) was added. The mixture was stirred at room temperature for 16 hours. The solvents were removed and residue was dissolved in water, washed with ether, then neutralized with 2N HCl to pH=3. 356 mg (73%) white solid was obtained after filtration and dried under vacuum. 1H NMR (400 MHz, DMSO) δ 12.90 (s, 1H), 8.27-8.17 (m, 2H), 7.29-7.19 (m, 2H), 6.80 (dd, J=2.9, 3.9 Hz, 1H), 5.02 (s, 2H), 2.85 (s, 3H). 13C NMR (101 MHz, DMSO, APT) δ 169.8, 154.5, 143.1, 141.4, 135.9, 123.9, 123.3, 122.8, 119.5, 113.3, 112.7, 41.6, 22.2. HRMS (m/z): calcd for C13H12N3O3 (M+H) 258.0879. found 258.0894.

Workup

  1. customThe solvents were removed
  2. dissolutionresidue was dissolved in water
  3. washwashed with ether

Sources & evidence

ORD record
ord-5b470fee8d3647829d7ebdd2eea241df
Source dataset
uspto-grants-2016_05
Patent number
US09345703B2

Reaction notes

Loading…