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

HRID 447126
Notes
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Reaction equation

HRID 447126 reaction equation
CON(C)[C:4]([C:6]1[N:7]=[CH:8][C:9]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[N:19]=[N:20][C:21]([CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[C:22]([CH3:25])[C:23]=3[CH3:24])[CH2:14][C@H:13]2[CH3:33])=[N:10][CH:11]=1)=[O:5].[CH3:35][Mg]I>C1COCC1>[CH2:26]([C:21]1[N:20]=[N:19][C:18]([N:15]2[CH2:16][CH2:17][N:12]([C:9]3[CH:8]=[N:7][C:6]([C:4](=[O:5])[CH3:35])=[CH:11][N:10]=3)[C@H:13]([CH3:33])[CH2:14]2)=[C:23]([CH3:24])[C:22]=1[CH3:25])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 59191539(R)-4-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-5'-carboxylic acid methoxy-methyl-amideHCID 178418373HCID 178418373, compound

Product 1

HCID 451071751-[(R)-4-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-5'-yl]-ethanoneYield 86.2%

Reagents, catalysts & solvents 1

HCID 8028Tetrahydrofuran
Solvent

Conditions

Temperature
0 °C

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 methoxy-methyl-amide (example 142, 450 mg, 0.975 mmol) is dissolved in THF (1 mL) and cooled to 0° C. A dropwise addition of methyl magnesium iodide (325 μL, 0.975 mmol) is added dropwise. Reaction is warmed to room temperature and continues to stir for 16 h. Add H2O (1 drop) and concentrate reaction mixture in vacuo. The residue is purified by flash chromatography on silica gel (60-100% EtOAc/Heptane and 0-8% MeOH/EtOAc) to afford the title compound (350 mg, 86%).

Workup

  1. additionis added dropwise
  2. customReaction
  3. temperatureis warmed to room temperature
  4. concentrationAdd H2O (1 drop) and concentrate
  5. customreaction mixture in vacuo
  6. customThe residue is purified by flash chromatography on silica gel (60-100% EtOAc/Heptane and 0-8% MeOH/EtOAc)

Sources & evidence

ORD record
ord-8ce2c8453c3844d4ae19d5585ea0d8a1
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08481542B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes