Ammonia → HCID 57990121、化合物

HRID 245610ノート

反応式

HRID 245610 の反応式
[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]

参加物

8

反応物 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

生成物 1

HCID 57990121HCID 57990121、化合物

試薬・触媒・溶媒 4

HCID 66133Benzyl triethylammonium chloride触媒HCID 313Hydrochloric Acid溶媒HCID 1140Toluene溶媒HCID 21939870Tetrahydrofuran ethyl acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a7c237c0c47946b1910931cdc8a235d7
出典データセット
uspto-grants-2014_02
特許番号
US08658801B2

反応ノート

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