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

HRID 81496

反応式

HRID 81496 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒2 回HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4ca20ac305394febb9a15d8950b4d4c1
出典データセット
uspto-grants-2014_09
特許番号
US08846687B2

関連ノート

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