Ammonium Chloride → AM6545

HRID 532244Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 532244
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([C:14]2[CH:19]=[CH:18][C:17](I)=[CH:16][CH:15]=2)=[C:12]([CH3:21])[C:11]([C:22]([NH:24][N:25]2[CH2:30][CH2:29][S:28](=[O:32])(=[O:31])[CH2:27][CH2:26]2)=[O:23])=[N:10]1.[C:33]([CH2:35][CH2:36][C:37]#[CH:38])#[N:34].[Cl-].[NH4+]>N1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:33]([CH2:35][CH2:36][C:37]#[C:38][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[N:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])[N:10]=[C:11]([C:22]([NH:24][N:25]3[CH2:30][CH2:29][S:28](=[O:32])(=[O:31])[CH2:27][CH2:26]3)=[O:23])[C:12]=2[CH3:21])=[CH:15][CH:16]=1)#[N:34]

Komponenten

6

Edukt 3

HCID 25517Ammonium ChlorideHCID 1405604-Cyano-1-butyneHCID 469129201-(2,4-dichlorophenyl)-4-methyl-5-(4-iodophenyl)-N-(1,1-dioxothiomorpholino)-1H-pyrazole-3-carboxamide

Produkt 1

HCID 46912919AM6545Ausbeute 43,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 31268PyrrolidineLösungsmittel2×

Versuchsvorschrift

To a stirred solution of amide obtained from step E (2 g, 3.3 mmol) in pyrrolidine (40 ml), under an argon atmosphere, tetrakis(triphenylphosphine)palladium(0) (0.4 g, 0.3 mmol) was added. The reaction mixture was stirred for 5 min at room temperature, and subsequently 4-cyano-1-butyne (0.78 g, 9.9 mmol) in pyrrolidine (1.5 ml) was added over 5 minutes. The resulting mixture was heated at 80-85° C. for 10 h. The reaction was hydrolyzed with a saturated aqueous solution of ammonium chloride and extracted with ethyl acetate. The organic extract was dried over MgSO4 and the solvent was removed in vacuo. Purification by flash column chromatography on silica gel (eluant ethylacetate) gave compound 15 as a white solid (0.8 g, 43.7%)

Aufarbeitung

  1. temperatureThe resulting mixture was heated at 80-85° C. for 10 h
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. dry with materialwas dried over MgSO4
  5. customthe solvent was removed in vacuo
  6. customPurification by flash column chromatography on silica gel (eluant ethylacetate)

Quellen und Nachweise

ORD-Eintrag
ord-88bceefa166843b9833a9897ebe786f2
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853205B2

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