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

HRID 81496
Notes
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Reaction equation

HRID 81496 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6344
Dichloromethane
Solvent
2×
HCID 80711,2-DimethoxyethaneSolvent
HCID 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-4ca20ac305394febb9a15d8950b4d4c1
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846687B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes