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Diisopropylethylamine → 5-Bromo-6-(4-fluoro-phenyl)-pyrazine-2-carboxylic acid (2-cyclopropyl-2-hydroxy-propyl)-amide

HRID 1865877
Notes
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Reaction equation

HRID 1865877 reaction equation
[Br:1][C:2]1[N:3]=[CH:4][C:5]([C:15]([OH:17])=O)=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1.ClC([N:23](C)C)=C(C)C.NC[CH2:28][C:29]([CH:32]1[CH2:34][CH2:33]1)([OH:31])[CH3:30].C(N(C(C)C)C(C)C)C>ClCCl>[CH:32]1([C:29]([OH:31])([CH3:30])[CH2:28][NH:23][C:15]([C:5]2[CH:4]=[N:3][C:2]([Br:1])=[C:7]([C:8]3[CH:9]=[CH:10][C:11]([F:14])=[CH:12][CH:13]=3)[N:6]=2)=[O:17])[CH2:34][CH2:33]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 688021404-Amino-2-cyclopropylbutan-2-olHCID 866169585-Bromo-6-(4-fluoro-phenyl)-pyrazine-2-carboxylic acid

Product 1

HCID 866169595-Bromo-6-(4-fluoro-phenyl)-pyrazine-2-carboxylic acid (2-cyclopropyl-2-hydroxy-propyl)-amideYield 68.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.78 g of 5-bromo-6-(4-fluoro-phenyl)-pyrazine-2-carboxylic acid in 15.0 ml dichloromethane was added at room temperature 0.39 g (1-chloro-2-methyl-propenyl)-dimethyl-amine and the mixture was stirred for 0.5 hours at room temperature. To the resulting white suspension was added 0.333 g 4-amino-2-cyclopropyl-butan-2-ol and 0.45 ml N-ethyldiisopropylamine and the mixture was stirred for 2 hours at room temperature. The resulting mixture was partitioned between 10% aqueous citric acid and dichloromethane. The phases were separated and the organic layer was dried over magnesium sulfate and evaporated. The residue was purified by chromatography on silica gel using a gradient of heptane to 25% ethyl acetate in heptane to yield 0.70 g of the title compound as white crystals. MS (ISP) (M+H+)=394.1 and 396.0.

Workup

  1. stirringthe mixture was stirred for 2 hours at room temperature
  2. customThe resulting mixture was partitioned between 10% aqueous citric acid and dichloromethane
  3. customThe phases were separated
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by chromatography on silica gel using a gradient of heptane to 25% ethyl acetate in heptane

Sources & evidence

ORD record
ord-bd02f1d47f994e9192658472b10f17d3
Source dataset
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07629346B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes