Ammonia → HCID 57990121, 화합물

HRID 245610노트

반응식

HRID 245610 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([NH:10][CH:11]([CH3:13])[CH3:12])=[O:9])[C:5]([NH:14][C:15]([C:17]2[N:21]([C:22]3[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][N:23]=3)[N:20]=[C:19]([C:29]([F:32])([F:31])[F:30])[CH:18]=2)=[O:16])=[C:4]([CH3:33])[CH:3]=1.[CH:34](=O)/[CH:35]=[CH:36]/[CH3:37].N>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.Cl.C1(C)C=CC=CC=1.C(OCC)(=O)C.O1CCCC1>[CH:11]([NH:10][C:8]([C:6]1[C:7]2[CH:34]=[CH:35][C:36]([CH3:37])=[N:1][C:2]=2[CH:3]=[C:4]([CH3:33])[C:5]=1[NH:14][C:15]([C:17]1[N:21]([C:22]2[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][N:23]=2)[N:20]=[C:19]([C:29]([F:32])([F:31])[F:30])[CH:18]=1)=[O:16])=[O:9])([CH3:13])[CH3:12]

참가 물질

8

반응물 3

HCID 222AmmoniaHCID 447466CrotonaldehydeHCID 10227689N-(4-amino-2-methyl-6-(((1-methylethyl)amino)carbonyl)phenyl)-1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide

생성물 1

HCID 57990121HCID 57990121, 화합물

시약·촉매·용매 4

HCID 66133Benzyl triethylammonium chloride촉매HCID 313Hydrochloric Acid용매HCID 1140Toluene용매HCID 21939870Tetrahydrofuran ethyl acetate용매

실험 절차

1.70 g (3.53 mMol) N-(4-amino-2-methyl-6-(((1-methylethyl)amino)carbonyl)phenyl)-1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide (known from WO 03/016284) and 41 mg (0.18 mmol) benzyltriethylammonium chloride in 35 mL conc. HCl and 35 mL toluene are vigorously stirred at 60° C. Then 0.58 mL (7 mmol) crotonaldehyde is added and the reaction mixture is stirred under reflux during 1 hour. The mixture is then cooled to ambient temperature, diluted with 10 mL ethyl acetate/tetrahydrofuran (1:1, v/v) and neutralised with an aqueous solution of concentrated ammonia. The organic phase is extracted and washed once with brine, then dried on Na2SO4, filtrated and evaporated. After column chromatography purification on silica gel with dichloromethane/tetrahydrofuran (3:1) as eluents, the compound is recrystallised from tetrahydrofuran/hexane to afford a colourless solid; LC/MS:531/533 (M+H)+, m.p.: >240° C.

후처리

  1. temperatureunder reflux during 1 hour
  2. extractionThe organic phase is extracted
  3. washwashed once with brine
  4. customdried on Na2SO4
  5. filtrationfiltrated
  6. customevaporated
  7. customAfter column chromatography purification on silica gel with dichloromethane/tetrahydrofuran (3:1) as eluents
  8. customthe compound is recrystallised from tetrahydrofuran/hexane
  9. customto afford a colourless solid

출처 및 근거

ORD 기록
ord-a7c237c0c47946b1910931cdc8a235d7
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658801B2

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