HCID 25152046, compound → HCID 68409139, compound

HRID 2066821Notes

Reaction equation

HRID 2066821 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:38]([CH3:40])[CH3:39])[C:6]2[O:10][C:9]([C:11]3[CH:36]=[CH:35][C:14]([C:15]([NH:17][CH2:18][C:19]4([CH3:34])[O:23][C:22](=[O:24])[N:21]([C:25]5[CH:30]=[CH:29][C:28]([N+:31]([O-])=O)=[CH:27][N:26]=5)[CH2:20]4)=[O:16])=[CH:13][CH:12]=3)=[N:8][C:7]=2[CH:37]=1)#[N:2].[H][H]>CO.O1CCCC1.[Pd]>[NH2:31][C:28]1[CH:29]=[CH:30][C:25]([N:21]2[CH2:20][C:19]([CH2:18][NH:17][C:15](=[O:16])[C:14]3[CH:13]=[CH:12][C:11]([C:9]4[O:10][C:6]5[C:5]([CH:38]([CH3:40])[CH3:39])=[CH:4][C:3]([C:1]#[N:2])=[CH:37][C:7]=5[N:8]=4)=[CH:36][CH:35]=3)([CH3:34])[O:23][C:22]2=[O:24])=[N:26][CH:27]=1

Participants

6

Reactant 2

HCID 25152046HCID 25152046, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68409139HCID 68409139, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)-N-{[5-methyl-3-(5-nitropyridin-2-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl}benzamide (154 mg, EXAMPLE 57) in 10 ml of methanol and 10 ml of tetrahydrofuran was added 50 mg of palladium on carbon (10% wet). The mixture was stirred at 40° C. under a balloon of hydrogen for 15 h. The sample was cooled to room temperature, and was filtered through a small plug of Celite, eluting with methanol. The eluent was concentrated and purified via column chromatography on a Biotage Horizon 40M column eluting with 0% ethyl acetate in hexanes (1 column volume), followed by a gradient to 100% ethyl acetate in hexanes (over 10 column volumes), and held at 100% ethyl acetate for 6 column volumes to provide the title compound (122 mg, 84%). Mass spectrum (ESI) 511.1 (M+1).

Workup

  1. filtrationwas filtered through a small plug of Celite
  2. washeluting with methanol
  3. concentrationThe eluent was concentrated
  4. custompurified via column chromatography on a Biotage Horizon 40M column
  5. washeluting with 0% ethyl acetate in hexanes (1 column volume)

Sources & evidence

ORD record
ord-69091b9cfe22415aa9e6c42400ccb89c
Source dataset
uspto-grants-2012_10
Patent number
US08293721B2

Reaction notes

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