Hydrochloric Acid → {9-Chloro-1-[6-methoxy-2-(trifluoromethyl)pyridin-3-yl]-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl}methanol

HRID 1629011Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1629011
[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([C:32](OC)=[O:33])=[C:11]2[C:15]=1[N:14]=[C:13]1[N:16]([C:20]3[C:21]([C:28]([F:31])([F:30])[F:29])=[N:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=3)[CH2:17][CH2:18][CH2:19][N:12]21.Cl.[Cl-].[NH4+]>C(O)C.O1CCCC1>[Cl:6][C:7]1[C:15]2[N:14]=[C:13]3[N:16]([C:20]4[C:21]([C:28]([F:30])([F:29])[F:31])=[N:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=4)[CH2:17][CH2:18][CH2:19][N:12]3[C:11]=2[C:10]([CH2:32][OH:33])=[CH:9][CH:8]=1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 57786121Methyl 9-chloro-1-[6-methoxy-2-(trifluoromethyl)pyridin-3-yl]-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylate

Produkt 1

HCID 57786319{9-Chloro-1-[6-methoxy-2-(trifluoromethyl)pyridin-3-yl]-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl}methanolAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of calcium chloride (670 mg, 6.04 mmol) in ethanol (15 mL) was added sodium tetrahydroborate (457 mg, 12.08 mmol) at 0° C. The mixture was stirred at 0° C. for 1 hr. A solution of methyl 9-chloro-1-[6-methoxy-2-(trifluoromethyl)pyridin-3-yl]-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylate (1.33 g, 3.02 mmol) in tetrahydrofuran (15 mL) was added dropwise to the mixture at 0° C. The mixture was stirred at 0° C. for 12 hr. 1N HCl (ca. 9.0 mL) was added to the reaction mixture at 0° C., and the aqueous ammonium chloride was added to the mixture. The solvent was removed in vacuo. The precipitated solid was collected by filtration, washed with water and diisopropyl ether to give the title compound (1.33 g, 3.02 mmol, quant) as a white solid.

Aufarbeitung

  1. stirringThe mixture was stirred at 0° C. for 12 hr
  2. customThe solvent was removed in vacuo
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with water and diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-b112e0beb3df40afb49cfa73838d26b5
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785460B2

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