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Sodium borohydride → 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)-3,4-dihydro-2H-benzo[f][1,4]oxazepin-5-one

HRID 1879685
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Reaktionsgleichung

Reaktionsgleichung von HRID 1879685
[C:1]([C:5]1[CH:47]=[CH:46][C:8]2[C:9](=[O:45])[N:10]([C:14]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]4[CH:27]=[C:26]([NH:28][C:29]5[CH:34]=[CH:33][C:32]([C:35]([N:37]6[CH2:42][CH2:41][O:40][CH2:39][CH2:38]6)=[O:36])=[CH:31][N:30]=5)[C:25](=[O:43])[N:24]([CH3:44])[CH:23]=4)[C:15]=3[CH:16]=[O:17])[CH2:11][CH2:12][O:13][C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)(C)C.C1COCC1>[C:1]([C:5]1[CH:47]=[CH:46][C:8]2[C:9](=[O:45])[N:10]([C:14]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]4[CH:27]=[C:26]([NH:28][C:29]5[CH:34]=[CH:33][C:32]([C:35]([N:37]6[CH2:42][CH2:41][O:40][CH2:39][CH2:38]6)=[O:36])=[CH:31][N:30]=5)[C:25](=[O:43])[N:24]([CH3:44])[CH:23]=4)[C:15]=3[CH2:16][OH:17])[CH2:11][CH2:12][O:13][C:7]=2[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]
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Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 595485232-(8-tert-Butyl-5-oxo-2,3-dihydro-5H-benzo[f][1,4]oxazepin-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 469451838-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)-3,4-dihydro-2H-benzo[f][1,4]oxazepin-5-oneAusbeute 54,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3776IsopropanolLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To 2-(8-tert-Butyl-5-oxo-2,3-dihydro-5H-benzo[f][1,4]oxazepin-4-yl)-6-{1-methyl-5-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-pyridin-3-yl}-benzaldehyde (0.27 mmol) in isopropanol (5 mL) and THF (10 mL) at 0 C with stirring was added sodium borohydride (21 mg, 2 eq) and then the ice bath was removed and the resulting mixture was stirred at room temperature for 45 minutes. TLC analysis indicated that the reaction was complete so the mixture was diluted with ethyl acetate (150 mL) and water (50 mL). The layers were partitioned, then separated and the organic layer was further washed with water (3×50 mL) and then finally washed with brine ((1×50 mL). The ethyl acetate layer was dried over magnesium sulfate, filtered and concentrated. Purification by Thin Layer Chromatography on silica gel eluting with 10% methanol in dichloromethane afforded the title compound as a light grey powder (94 mg), (M+H)+=638.

Aufarbeitung

  1. customthe ice bath was removed
  2. additionwas diluted with ethyl acetate (150 mL) and water (50 mL)
  3. customThe layers were partitioned
  4. customseparated
  5. washthe organic layer was further washed with water (3×50 mL)
  6. washfinally washed with brine ((1×50 mL)
  7. dry with materialThe ethyl acetate layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by Thin Layer Chromatography on silica gel eluting with 10% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-6af2d96a5e8f4c0898b653942ae0ddcf
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08318719B2

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