Ethanol → 8-tert-Butyl-4-(2-hydroxymethyl-3-{1-methyl-5-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-pyridin-3-yl}-phenyl)-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one

HRID 1879687Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1879687
[C:1]([C:5]1[CH:6]=[CH:7][C:8]2[C:14](=[O:15])[N:13]([C:16]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]4[CH:29]=[C:28]([NH:30][C:31]5[CH:36]=[CH:35][C:34]([C:37]([N:39]6[CH2:44][CH2:43][O:42][CH2:41][CH2:40]6)=[O:38])=[CH:33][N:32]=5)[C:27](=[O:45])[N:26]([CH3:46])[CH:25]=4)[C:17]=3[CH:18]=[O:19])[CH2:12][CH2:11][NH:10][C:9]=2[CH:47]=1)([CH3:4])([CH3:3])[CH3:2].C(O)C.[BH4-].[Na+]>C1COCC1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]2[C:14](=[O:15])[N:13]([C:16]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]4[CH:29]=[C:28]([NH:30][C:31]5[CH:36]=[CH:35][C:34]([C:37]([N:39]6[CH2:44][CH2:43][O:42][CH2:41][CH2:40]6)=[O:38])=[CH:33][N:32]=5)[C:27](=[O:45])[N:26]([CH3:46])[CH:25]=4)[C:17]=3[CH2:18][OH:19])[CH2:12][CH2:11][NH:10][C:9]=2[CH:47]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 595485292-(8-tert-Butyl-5-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-6-{1-methyl-5-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-pyridin-3-yl}-benzaldehyde

Produkt 1

HCID 469451828-tert-Butyl-4-(2-hydroxymethyl-3-{1-methyl-5-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-pyridin-3-yl}-phenyl)-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The 60:40 mixture from the previous step, with the major component being 2-(8-tert-Butyl-5-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-6-{1-methyl-5-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-pyridin-3-yl}-benzaldehyde, 76 mg, was dissolved in 3 mL THF, and 3 mL absolute ethanol was added. Sodium borohydride (5 mg, 1 eq), was added, and the reaction stirred for 20 minutes, during which time the reaction changed from purple color to colorless. The reaction as quenched with water, and then 1 drop glacial acetic acid was added. The mixture was extracted with ethyl acetate 3×, the organic layers combined and washed with aqueous saturated sodium bicarbonate solution and brine, dried over MgSO4, filtered, and the organic solvent removed under vacuum. The residue was chromatographed over silica gel, eluting first with methylene chloride, and then 3% methanol in methylene chloride, to give the title compound as a white solid, 33 mg, (M+H)+=637.

Aufarbeitung

  1. customThe reaction
  2. customas quenched with water
  3. addition1 drop glacial acetic acid was added
  4. extractionThe mixture was extracted with ethyl acetate 3×
  5. washwashed with aqueous saturated sodium bicarbonate solution and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customthe organic solvent removed under vacuum
  9. customThe residue was chromatographed over silica gel
  10. washeluting first with methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-779ecac7d0da4d6da200ff6817e375f2
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318719B2

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