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

HRID 2387226

반응식

HRID 2387226 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 6344Dichloromethane용매2회HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-06aca14707174b80bf8a02755af6e412
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268834B2

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