Sodium borohydride → N-(5-(3,5-Difluorobenzyl)-1H-indazol-3-yl)-4-(4-methylpiperazin-1-yl)-2-nitrobenzamide

HRID 1186577Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1186577
[F:1][C:2]1[CH:3]=[C:4]([CH:35]=[C:36]([F:38])[CH:37]=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:16][C:17](=[O:34])[C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)=[CH:20][C:19]=1[N+:31]([O-:33])=[O:32])=O.[BH4-].[Na+]>C(Cl)Cl.FC(F)(F)C(O)=O>[F:38][C:36]1[CH:35]=[C:4]([CH:3]=[C:2]([F:1])[CH:37]=1)[CH2:5][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[C:10]2[NH:16][C:17](=[O:34])[C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:25][CH2:26][N:27]([CH3:30])[CH2:28][CH2:29]2)=[CH:20][C:19]=1[N+:31]([O-:33])=[O:32]

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 68671073N-(5-(3,5-Difluorobenzoyl)-1H-indazol-3-yl)-4-(4-methylpiperazin-1-yl)-2-nitrobenzamide

Produkt 1

HCID 25175858N-(5-(3,5-Difluorobenzyl)-1H-indazol-3-yl)-4-(4-methylpiperazin-1-yl)-2-nitrobenzamideAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

N-[5-(3,5-Difluoro-benzoyl)-1H-indazol-3-yl]-4-(4-methyl-piperazin-1-yl)-2-nitro-benzamide (3.61 g, 6.93 mmol) was dissolved in DCM (150 mL) in argon atmosphere and trifluoroacetic acid (150 mL) is added under stirring. Sodium borohydride pellets (2.62 gr, 69.3 mmol) is gradually added over a period of 72 hours. The reaction mixture was evaporated, taken up with a mixture MeOH/acetone and stirred for 1 hour. The resulting mixture was evaporated to dryness, redissolved in MeOH and NaOH 8N was added till basic pH was reached. Crude was evaporated and ice/water was added, the solid thus formed was filtered, washed with water and dried under vacuum at 80° C. affording 3.22 g of title compound (92% yield).

Aufarbeitung

  1. additionis added
  2. additionis gradually added over a period of 72 hours
  3. customThe reaction mixture was evaporated
  4. stirringstirred for 1 hour
  5. customThe resulting mixture was evaporated to dryness
  6. dissolutionredissolved in MeOH
  7. additionNaOH 8N was added till basic pH
  8. customCrude was evaporated
  9. additionice/water was added
  10. customthe solid thus formed
  11. filtrationwas filtered
  12. washwashed with water
  13. customdried under vacuum at 80° C.

Quellen und Nachweise

ORD-Eintrag
ord-a189e4e202684397aa6d1afd4698ee79
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673893B2

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