Lithium hydroxide, monohydrate → Lithium 2-(2-(2-(2-((4-(1-(tert-butoxycarbonyl)piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)-4-fluorophenyl)acetate

HRID 1779015Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1779015
O[Li:2].O.[F:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:43][C:44]([O:46]C)=[O:45])=[C:9]([CH:42]=1)[CH2:10][CH2:11][C:12]1[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][N:15]=[C:14]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([CH:29]3[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH2:30]3)=[CH:25][CH:24]=2)[N:13]=1>O.C1COCC1>[C:38]([O:37][C:35]([N:32]1[CH2:31][CH2:30][CH:29]([C:26]2[CH:25]=[CH:24][C:23]([NH:22][C:14]3[N:13]=[C:12]([CH2:11][CH2:10][C:9]4[CH:42]=[C:5]([F:4])[CH:6]=[CH:7][C:8]=4[CH2:43][C:44]([O-:46])=[O:45])[C:17]([C:18]([F:19])([F:20])[F:21])=[CH:16][N:15]=3)=[CH:28][CH:27]=2)[CH2:34][CH2:33]1)=[O:36])([CH3:41])([CH3:39])[CH3:40].[Li+:2]

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 86712666tert-Butyl 4-(4-((4-(5-fluoro-2-(2-methoxy-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate

Produkt 1

HCID 86712667Lithium 2-(2-(2-(2-((4-(1-(tert-butoxycarbonyl)piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)-4-fluorophenyl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

LiOH.H2O (0.063 g, 1.5 mmol) was added to a stirred solution of tert-butyl 4-(4-((4-(5-fluoro-2-(2-methoxy-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate (A52) (0.092 g, 0.15 mmol) in H2O (0.5 mL) and THF (5 mL) and the resulting mixture heated at 40° C. overnight. The volatiles were removed in vacuo and the residue was taken up in DCM (50 mL). The resulting solution was washed with saturated aqueous Na2CO3 (25 mL) then the aqueous phase was then extracted with DCM (2×25 mL). The organic layers were combined, dried over MgSO4 and the volatiles were removed in vacuo to yield the title compound A53 (0.089 g, 98%); LCMS-A: rt 6.596 min; m/z 603 [(M-Li)+H]+.

Aufarbeitung

  1. customThe volatiles were removed in vacuo
  2. washThe resulting solution was washed with saturated aqueous Na2CO3 (25 mL)
  3. extractionthe aqueous phase was then extracted with DCM (2×25 mL)
  4. dry with materialdried over MgSO4
  5. customthe volatiles were removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cbfe8206618b44b69c87de8e00994969
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09266864B2

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