2-Methylpentane → 3-Chloro-5-[2-methyl-5-(morpholine-4-sulfonyl)-phenyl]-pyrazin-2-ylamine

HRID 2387226

Reaction equation

HRID 2387226 reaction equation
Br[C:2]1[N:3]=[C:4]([Cl:9])[C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)(=[O:19])=[O:18])=[CH:13][C:12]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].CCCC(C)C>C(Cl)Cl.C(OCC)(=O)C.COCCOC>[Cl:9][C:4]1[C:5]([NH2:8])=[N:6][CH:7]=[C:2]([C:12]2[CH:13]=[C:14]([S:17]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)(=[O:19])=[O:18])[CH:15]=[CH:16][C:11]=2[CH3:10])[N:3]=1

Participants

8

Reactant 4

HCID 78922-MethylpentaneHCID 10340Sodium CarbonateHCID 441195542-Methyl-5-(morpholin-4-ylsulphonyl)benzeneboronic acidHCID 467382025-Bromo-3-chloropyrazin-2-amine

Product 1

HCID 866345543-Chloro-5-[2-methyl-5-(morpholine-4-sulfonyl)-phenyl]-pyrazin-2-ylamine

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolvent2×HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Bromo-3-chloro-pyrazin-2-ylamine (0.600 g, 2.88 mmol), 2-methyl-5-(N-morpholinylsulfonyl)phenylboronic acid (0.821 g, 2.88 mmol), 1,1′BIS(Diphenylphosphino-ferrocene)dichloropalladium (II) complex with DCM (0.118 g, 0.14 mmol), 2N Na2CO3 (aq.) (5 ml) and DME (15 ml) are stirred together at 100° C. for 1 hour. Product is purified by reverse phase chromatography and evaporation of the clean fractions yields a cream solid. The solid is dissolved in DCM (100 ml) and washed with 2N NaOH (aq.) (50 ml). The organic phase is dried over magnesium sulphate, filtered and the solvent evaporated to yield an orange semi-solid. This is dissolved ethyl acetate (10 ml) and iso-hexane is added. A precipitate forms and is filtered off to yield the title compound as an off white solid. [M+H]+ 410.

Workup

  1. customProduct is purified by reverse phase chromatography and evaporation of the clean fractions
  2. customyields a cream solid
  3. washwashed with 2N NaOH (aq.) (50 ml)
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent evaporated
  7. customto yield an orange semi-solid
  8. additionis added
  9. filtrationA precipitate forms and is filtered off

Sources & evidence

ORD record
ord-06aca14707174b80bf8a02755af6e412
Source dataset
uspto-grants-2012_09
Patent number
US08268834B2

Linked notes

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