Benzyl [(4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)methyl]methylcarbamate → HCID 68584728, compound

HRID 17560Notes

Reaction equation

HRID 17560 reaction equation
[C:1]([C:3]1[C:8]2[N:9]=[C:10]([CH2:12][N:13](C)[C:14](=O)OCC3C=CC=CC=3)[O:11][C:7]=2[C:6]([F:25])=[C:5]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:4]=1[CH3:32])#[N:2]>[C].[Pd].C(O)C>[F:25][C:6]1[C:5]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:4]([CH3:32])[C:3]([C:1]#[N:2])=[C:8]2[C:7]=1[O:11][C:10]([CH2:12][NH:13][CH3:14])=[N:9]2

Participants

4

Reactant 1

HCID 86630878Benzyl [(4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)methyl]methylcarbamate

Product 1

HCID 68584728HCID 68584728, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A catalyst 10% palladium-carbon (100 mg) was added to an ethanol (6 ml) solution of benzyl [(4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)methyl]methylcarbamate (I-272) (242 mg, 0.564 mmol), followed by stirring under hydrogen atmosphere at room temperature for 6 hours. The insoluble matter was separated by filtration, the filtrate was concentrated, and the resulting residue was purified by silica gel column chromatography (eluent, chloroform:methanol=10:1, v/v) to obtain the entitled compound (115 mg, 69%) as a colorless oily substance.

Workup

  1. customThe insoluble matter was separated by filtration
  2. concentrationthe filtrate was concentrated
  3. customthe resulting residue was purified by silica gel column chromatography (eluent, chloroform

Sources & evidence

ORD record
ord-f72d6fca2f54463ca51f2267d4b11988
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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