Sodium Hydroxide → 2,4-Difluoro-N-[5-[4-(5-{[4-(1-methylethyl)-1-piperazinyl]methyl}-1,3-oxazol-2-yl)-1H-indazol-6-yl]-2-(methyloxy)-3-pyridinyl]benzenesulfonamide

HRID 2036063Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2036063
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[C:14]([O:52][CH3:53])=[N:15][CH:16]=[C:17]([C:19]2[CH:27]=[C:26]3[C:22]([CH:23]=[N:24][N:25]3S(C3C=CC=CC=3)(=O)=O)=[C:21]([C:37]3[O:38][C:39]([CH2:42][N:43]4[CH2:48][CH2:47][N:46]([CH:49]([CH3:51])[CH3:50])[CH2:45][CH2:44]4)=[CH:40][N:41]=3)[CH:20]=2)[CH:18]=1)(=[O:11])=[O:10].[OH-].[Na+]>C(O)(C)C.CO>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[C:14]([O:52][CH3:53])=[N:15][CH:16]=[C:17]([C:19]2[CH:27]=[C:26]3[C:22]([CH:23]=[N:24][NH:25]3)=[C:21]([C:37]3[O:38][C:39]([CH2:42][N:43]4[CH2:44][CH2:45][N:46]([CH:49]([CH3:50])[CH3:51])[CH2:47][CH2:48]4)=[CH:40][N:41]=3)[CH:20]=2)[CH:18]=1)(=[O:10])=[O:11]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 595647092,4-Difluoro-N-[5-[4-(5-{[4-(1-methylethyl)-1-piperazinyl]methyl}-1,3-oxazol-2-yl)-1-(phenylsulfonyl)-1H-indazol-6-yl]-2-(methyloxy)-3-pyridinyl]benzenesulfonamide

Produkt 1

HCID 497839262,4-Difluoro-N-[5-[4-(5-{[4-(1-methylethyl)-1-piperazinyl]methyl}-1,3-oxazol-2-yl)-1H-indazol-6-yl]-2-(methyloxy)-3-pyridinyl]benzenesulfonamideAusbeute 68,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

2,4-Difluoro-N-[5-[4-(5-{[4-(1-methylethyl)-1-piperazinyl]methyl}-1,3-oxazol-2-yl)-1-(phenylsulfonyl)-1H-indazol-6-yl]-2-(methyloxy)-3-pyridinyl]benzenesulfonamide (81 mg, 0.106 mmol) was suspended in isopropanol (2 ml) and 2M sodium hydroxide (aq) (0.53 ml, 1.060 mmol) was added. The reaction mixture was stirred at RT for 2 h, the solvent removed and the residue dissolved in water (1 ml) and acidified to pH˜6 by the addition of 2M hydrogen chloride (aq). The resultant suspension was extracted with dichloromethane (3×2 ml), the organic layer separated (hydrophobic frit) and concentrated in vacuo to give a brown solid which dissolved in MeOH:DMSO (1 ml, 1:1, v/v) and purified by MDAP (method A). The appropriate fractions were concentrated in vacuo to give the title compound as a white solid (45 mg).

Aufarbeitung

  1. customthe solvent removed
  2. dissolutionthe residue dissolved in water (1 ml)
  3. additionacidified to pH˜6 by the addition of 2M hydrogen chloride (aq)
  4. extractionThe resultant suspension was extracted with dichloromethane (3×2 ml)
  5. customthe organic layer separated (hydrophobic frit)
  6. concentrationconcentrated in vacuo
  7. customto give a brown solid which
  8. customDMSO (1 ml, 1:1, v/v) and purified by MDAP (method A)
  9. concentrationThe appropriate fractions were concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f9663b4f2d0145ef924301b73459b491
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575162B2

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