Lithium Hydroxide → (S)-4-(4-((6-oxo-6,6a,7,8,9,10-hexahydro-5H-dipyrido [1,2-a:3',2'-e]pyrazin-3-yl)methyl)piperazin-1-yl)benzoic acid

HRID 716257Notes

Reaction equation

HRID 716257 reaction equation
[O:1]=[C:2]1[NH:7][C:6]2[CH:8]=[C:9]([CH2:12][N:13]3[CH2:18][CH2:17][N:16]([C:19]4[CH:28]=[CH:27][C:22]([C:23]([O:25]C)=[O:24])=[CH:21][CH:20]=4)[CH2:15][CH2:14]3)[CH:10]=[N:11][C:5]=2[N:4]2[CH2:29][CH2:30][CH2:31][CH2:32][C@@H:3]12.[Li+].[OH-]>O1CCOCC1>[O:1]=[C:2]1[NH:7][C:6]2[CH:8]=[C:9]([CH2:12][N:13]3[CH2:14][CH2:15][N:16]([C:19]4[CH:28]=[CH:27][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=4)[CH2:17][CH2:18]3)[CH:10]=[N:11][C:5]=2[N:4]2[CH2:29][CH2:30][CH2:31][CH2:32][C@@H:3]12

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66774897(S)-methyl 4-(4-((6-oxo-6,6a,7,8,9,10-hexahydro-5H-dipyrido[1,2-a:3',2'-e]pyrazin-3-yl)methyl)piperazin-1-yl)benzoate

Product 1

HCID 58324508(S)-4-(4-((6-oxo-6,6a,7,8,9,10-hexahydro-5H-dipyrido [1,2-a:3',2'-e]pyrazin-3-yl)methyl)piperazin-1-yl)benzoic acidYield 83.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(S)-methyl 4-(4-((6-oxo-6,6a,7,8,9,10-hexahydro-5H-dipyrido[1,2-a:3′,2′-e]pyrazin-3-yl)methyl)piperazin-1-yl)benzoate (152 mg, 0.349 mmol) was taken up in dioxane (2 ml) and LiOH (1N, 2 ml, 2.000 mmol) was added. The reaction was stirred 16 h at room temperature. The reaction was concentrated in-vacuo and the residue was taken up in water (5 mL) and acidified (4.5N HCl) to pH 4. A white precipitate formed. The precipitate was filtered off and dried in vacuum to afford the title compound (122.8 mg, 83%) as a white solid. [M+H] calc'd for C23H27N5O3, 422. found, 422.

Workup

  1. concentrationThe reaction was concentrated in-vacuo
  2. customA white precipitate formed
  3. filtrationThe precipitate was filtered off
  4. customdried in vacuum

Sources & evidence

ORD record
ord-7033891083a84d6fa657f009b5632fb4
Source dataset
uspto-grants-2015_11
Patent number
US09187497B2

Reaction notes

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