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Sodium Hydroxide → HCID 86608448, compound

HRID 551874
Notes
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Reaction equation

HRID 551874 reaction equation
[C:1]([C:5]1[CH:38]=[CH:37][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[N:19]=[C:20]([NH:26][C:27]4[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][OH:35])=[CH:29][CH:28]=4)[C:21](=[O:25])[N:22]([CH3:24])[CH:23]=3)[C:13]=2[CH3:36])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[S:48](Cl)([CH3:51])(=[O:50])=[O:49].[OH-].[Na+]>C(Cl)Cl>[C:1]([C:5]1[CH:38]=[CH:37][C:8]([C:9]([NH:11][C:12]2[C:13]([CH3:36])=[C:14]([C:18]3[N:19]=[C:20]([NH:26][C:27]4[CH:28]=[CH:29][C:30]([CH2:33][CH2:34][O:35][S:48]([CH3:51])(=[O:50])=[O:49])=[CH:31][CH:32]=4)[C:21](=[O:25])[N:22]([CH3:24])[CH:23]=3)[CH:15]=[CH:16][CH:17]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 58729053HCID 58729053, compound

Product 1

HCID 86608448HCID 86608448, compound

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Procedure

A solution of 5-bromo-3-[4-(2-hydroxy-ethyl)-phenylamino]-1-methyl-1H-pyrazin-2-one (2) (1.2 g; 2.35 mmol) in CH2Cl2 (30 mL) was cooled to 0° C. and 1.5 mL of diisopropylethyl amine was added. A second solution containing 0.75 mL mesyl chloride in 3 mL CH2Cl2 was added dropwise to the stirring reaction solution under N2 and the reaction allowed to warm to rt for 1 hr. 0.1N Sodium hydroxide was then added carefully to the reaction, and the layers separated. The CH2Cl2 layer was washed with brine and dried over solid sodium sulfate, then filtered and evaporated to a light red-brown oil (1.5 g). The crude methanesulfonic acid 2-(4-{6-[3-(4-tert-butyl-benzoylamino)-2-methyl-phenyl]-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino}-phenyl)-ethyl ester (3) was used directly in subsequent reactions.

Workup

  1. additionwas added dropwise to the stirring reaction solution under N2
  2. customthe layers separated
  3. washThe CH2Cl2 layer was washed with brine
  4. dry with materialdried over solid sodium sulfate
  5. filtrationfiltered
  6. customevaporated to a light red-brown oil (1.5 g)

Sources & evidence

ORD record
ord-b8914a4da85244f99c34d11584474c91
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07947835B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes