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

HRID 1865880Notes

Reaction equation

HRID 1865880 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]([Cl:14])=[CH:10][CH:9]=1.ClC(N(C)C)=C(C)C.[NH2:26][CH2:27][C:28]([CH:31]1[CH2:33][CH2:32]1)([OH:30])[CH3:29].C(N(C(C)C)C(C)C)C>ClCCl>[CH:31]1([C:28]([OH:30])([CH3:29])[CH2:27][NH:26][C:15]([C:5]2[CH:4]=[N:3][C:2]([Br:1])=[C:7]([C:8]3[CH:9]=[CH:10][C:11]([Cl:14])=[CH:12][CH:13]=3)[N:6]=2)=[O:17])[CH2:33][CH2:32]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 211096921-Amino-2-cyclopropylpropan-2-olHCID 866169645-Bromo-6-(4-chloro-phenyl)-pyrazine-2-carboxylic acid

Product 1

HCID 866169635-Bromo-6-(4-chloro-phenyl)-pyrazine-2-carboxylic acid (2-cyclopropyl-2-hydroxy-propyl)-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 0.700 g (0.00223 mol) 5-bromo-6-(4-chloro-phenyl)-pyrazine-2-carboxylic acid in 7.0 ml dichloromethane was added a solution of 0.35 g (0.00262 mol) (1-chloro-2-methyl-propenyl)-dimethyl-amine and the mixture was stirred at room temperature for 45 min. To the resulting yellow solution was added dropwise during 15 minutes a solution of 0.296 g (0.00257 mol) 1-amino-2-cyclopropyl-propan-2-ol and 0.433 g ethyldiisopropylamine in 4.0 ml dichloromethane and the mixture was stirred at room temperature for 1 h. The resulting mixture was partitioned between 10% aqueous citric acid and ethyl acetate. The phases were separated and the organic phase was dried over magnesium sulfate and evaporated. The residue was purified by chromatography on silica gel with heptane to ethyl acetate=7:3 to yield 0.748 g (81% Th) of the title compound as slightly yellow foam. MS (ISP) (M+H+)=410.1 and 412.0.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 h
  2. customThe resulting mixture was partitioned between 10% aqueous citric acid and ethyl acetate
  3. customThe phases were separated
  4. dry with materialthe organic phase was dried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by chromatography on silica gel with heptane to ethyl acetate=7:3

Sources & evidence

ORD record
ord-c15b41e980bb438291b90455e9cc157e
Source dataset
uspto-grants-2009_12
Patent number
US07629346B2

Reaction notes

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