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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
Notes
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Reaction equation

HRID 1879685 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 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

Product 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-oneYield 54.6%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolvent
HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6af2d96a5e8f4c0898b653942ae0ddcf
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08318719B2

Reaction notes

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