Sodium Hydroxide → 5-(4-((Piperidin-4-ylmethyl)carbamoyl)phenylamino)-2-(2,6-difluorophenyl)oxazole-4-carboxamide

HRID 714990Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 714990
[C:1]([C:3]1[N:4]=[C:5]([C:32]2[C:37]([F:38])=[CH:36][CH:35]=[CH:34][C:33]=2[F:39])[O:6][C:7]=1[NH:8][C:9]1[CH:31]=[CH:30][C:12]([C:13]([NH:15][CH2:16][CH:17]2[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]2)=[O:14])=[CH:11][CH:10]=1)#[N:2].C(=O)(O)[O-:41].[Na+].[OH-].[Na+]>S(=O)(=O)(O)O>[NH:20]1[CH2:19][CH2:18][CH:17]([CH2:16][NH:15][C:13]([C:12]2[CH:30]=[CH:31][C:9]([NH:8][C:7]3[O:6][C:5]([C:32]4[C:37]([F:38])=[CH:36][CH:35]=[CH:34][C:33]=4[F:39])=[N:4][C:3]=3[C:1]([NH2:2])=[O:41])=[CH:10][CH:11]=2)=[O:14])[CH2:22][CH2:21]1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 59587428Tert-butyl 4-((4-(4-cyano-2-(2,6-difluorophenyl)oxazol-5-ylamino)benzamido)methyl)piperidine-1-carboxylate

Produkt 1

HCID 595875095-(4-((Piperidin-4-ylmethyl)carbamoyl)phenylamino)-2-(2,6-difluorophenyl)oxazole-4-carboxamideAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

A solution of tert-butyl 4-((4-(4-cyano-2-(2,6-difluorophenyl)oxazol-5-ylamino)benzamido)methyl)piperidine-1-carboxylate (0.028 g, 0.052 mmol) in concentrated sulfuric acid (1 mL) was stirred at room temperature for 1.5 hours. The solution was neutralised by pouring into saturated sodium bicarbonate solution. The aqueous phase was then basified to pH14 with 5M NaOH and extracted with EtOAc. The combined organic phases were dried over MgSO4 and the solvent removed in vacuo to afford 5-(4-((piperidin-4-ylmethyl)carbamoyl)phenylamino)-2-(2,6-difluorophenyl)oxazole-4-carboxamide (0.003 g, 0.007 mmol, 14%) as a yellow solid. 1H NMR (CD3OD) δ 1.51 (2H, m), 2.00 (3H, m), 2.99 (2H, t), 3.35 (2H, m), 3.45 (2H, m), 7.22 (2H, t), 7.53 (2H, d), 7.60 (1H, m), 7.87 (2H, d), 8.55 (1H, br s). LCMS (2) Rt: 1.85 min; m/z (ES+) 456.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-72565371665642c08274e4bcf22e92d9
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187465B2

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