Trifluoroacetic acid → N-(5-(3,5-Difluorobenzoyl)-1H-indazol-3-yl)-4-(4-methylpiperazin-1-yl)-2-nitrobenzamide

HRID 571894Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 571894
[F:1][C:2]1[CH:3]=[C:4]([CH:54]=[C:55]([F:57])[CH:56]=1)[C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12](C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[N:11]=[C:10]2[NH:35][C:36](=[O:53])[C:37]1[CH:42]=[CH:41][C:40]([N:43]2[CH2:48][CH2:47][N:46]([CH3:49])[CH2:45][CH2:44]2)=[CH:39][C:38]=1[N+:50]([O-:52])=[O:51])=[O:6].FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:54]=[C:55]([F:57])[CH:56]=1)[C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[C:10]2[NH:35][C:36](=[O:53])[C:37]1[CH:42]=[CH:41][C:40]([N:43]2[CH2:44][CH2:45][N:46]([CH3:49])[CH2:47][CH2:48]2)=[CH:39][C:38]=1[N+:50]([O-:52])=[O:51])=[O:6]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 68671004N-(5-(3,5-Difluorobenzoyl)-1-trityl-1H-indazol-3-yl)-4-(4-methylpiperazin-1-yl)-2-nitrobenzamide

Produkt 1

HCID 68671073N-(5-(3,5-Difluorobenzoyl)-1H-indazol-3-yl)-4-(4-methylpiperazin-1-yl)-2-nitrobenzamideAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of N-[5-(3,5-Difluoro-benzoyl)-1-trityl-1H-indazol-3-yl]-4-(4-methyl-piperazin-1-yl)-2-nitro-benzamide (2.76 g, 3.62 mmol), trifluoroacetic acid (5.6 mL) and dichloromethane (56 mL) was stirred at room temperature for 2 hours. The volatiles were evaporated and the residue taken up with dichloromethane and washed with a saturated solution of sodium hydrogen-carbonate. The organic phase was evaporated to dryness. The residue was redissolved in ethyl acetate and washed twice with brine. The resulting organic phase was dried over sodium sulfate and evaporated to dryness. Purification of the crude by chromatography over silica gel (DCM/MeOH) and trituration of the so obtained compound from diethyl ether afforded 1.47 g of the title compound (78% yield).

Aufarbeitung

  1. customThe volatiles were evaporated
  2. washwashed with a saturated solution of sodium hydrogen-carbonate
  3. customThe organic phase was evaporated to dryness
  4. dissolutionThe residue was redissolved in ethyl acetate
  5. washwashed twice with brine
  6. dry with materialThe resulting organic phase was dried over sodium sulfate
  7. customevaporated to dryness
  8. customPurification of the crude by chromatography over silica gel (DCM/MeOH) and trituration of the so obtained compound from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-0bd3c2d5871243dbbeeda238cf1a2cf1
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029356B2

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