Sodium borohydride → Ethyl 1-[5-[2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-7-(hydroxymethyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate

HRID 712322Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 712322
[CH2:1]([N:3]1[CH2:8][N:7]([CH3:9])[CH2:6][N:5]([C:10]2[S:11][C:12]3[C:18]([CH:19]=[O:20])=[CH:17][C:16]([C:21]4[CH:22]=[N:23][C:24]([N:27]5[CH2:32][CH2:31][C:30]([CH3:38])([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:29][CH2:28]5)=[N:25][CH:26]=4)=[CH:15][C:13]=3[N:14]=2)[C:4]1=[O:39])[CH3:2].[BH4-].[Na+]>CCO.C(Cl)Cl.CCOC(C)=O>[CH2:1]([N:3]1[CH2:8][N:7]([CH3:9])[CH2:6][N:5]([C:10]2[S:11][C:12]3[C:18]([CH2:19][OH:20])=[CH:17][C:16]([C:21]4[CH:22]=[N:23][C:24]([N:27]5[CH2:28][CH2:29][C:30]([CH3:38])([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:31][CH2:32]5)=[N:25][CH:26]=4)=[CH:15][C:13]=3[N:14]=2)[C:4]1=[O:39])[CH3:2]

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 86664036Ethyl 1-[5-[2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-7-formyl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate

Produkt 1

HCID 66977202Ethyl 1-[5-[2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-7-(hydroxymethyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylateAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 21584144Dichloromethane ethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Ethyl 1-[5-[2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-7-formyl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (560 mg, 1.02 mmol) was dissolved in 1:1 EtOH/CH2Cl2 (40 mL) and cooled to 0° C. NaBH4 (77 mg, 2.03 mmol) was added and the mixture allowed to warm to rt with stirring for 2 h. The mixture was diluted with EtOAc (200 mL), washed with water, brine and separated. The organic fraction was dried (Na2SO4) and concentrated under reduced pressure to afford the desired compound (484 mg, 86%) as a white solid. MS: 554.12 [M+H]+.

Aufarbeitung

  1. temperatureto warm to rt
  2. washwashed with water, brine
  3. customseparated
  4. dry with materialThe organic fraction was dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-aa98f7b42fa240f8aaff7faed3ac20a9
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181234B2

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