HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Water → (R)-4-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-5'-carboxylic acid

HRID 1480001
Notes
Print preview

Reaction equation

HRID 1480001 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[N:18]=[N:19][C:20]([CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[C:21]([CH3:24])[C:22]=3[CH3:23])[CH2:13][C@H:12]2[CH3:32])=[N:9][CH:10]=1)=[O:4].[Li+].[OH-].O.C1COCC1>CO>[CH2:25]([C:20]1[N:19]=[N:18][C:17]([N:14]2[CH2:15][CH2:16][N:11]([C:8]3[CH:7]=[N:6][C:5]([C:3]([OH:4])=[O:2])=[CH:10][N:9]=3)[C@H:12]([CH3:32])[CH2:13]2)=[C:22]([CH3:23])[C:21]=1[CH3:24])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 59191561(R)-Methyl 5-(4-(6-benzyl-4,5-dimethylpyridazin-3-yl)-2-methylpiperazin-1-yl)pyrazine-2-carboxylate

Product 1

HCID 59191562(R)-4-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-5'-carboxylic acidYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-4-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-5′-carboxylic acid methyl ester (1.8 g, 4.16 mmol) is combined with LiOH (998 mg, 42 mmol), H2O (20 mL), THF (20 mL), and MeOH (10 mL). The combined mixture is allowed to stir at room temperature for 16 h. It is concentrated to remove organic solvents in vacuo. Additional water is added and the pH is adjusted to 4.0 with HCl or phosphate buffer. The solution is extracted with EtOAc and the combined organic extracts are washed with brine. The extract is dried over sodium sulfate and filtered to remove the drying agent. The filtrate is concentrated to afford the title compound (1.46 g, 84%).

Workup

  1. concentrationIt is concentrated
  2. customto remove organic solvents in vacuo
  3. additionAdditional water is added
  4. extractionThe solution is extracted with EtOAc
  5. washthe combined organic extracts are washed with brine
  6. dry with materialThe extract is dried over sodium sulfate
  7. filtrationfiltered
  8. customto remove the drying agent
  9. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-0a0cde7cc99841b98fb658dc15d96c4b
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09409871B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes