HCID 178418361, compound → HCID 178454000, compound

HRID 906051Notes

Reaction equation

HRID 906051 reaction equation
[C:1]([C:3]1[CH:18]=[CH:17][C:6]([C:7]([O:9]CC2C=CC=CC=2)=[O:8])=[CH:5][C:4]=1[NH:19][C@H:20]1[CH2:25][CH2:24][C@H:23]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22][CH2:21]1)#[N:2].[H][H]>[Pd].C(OCC)(=O)C.CO>[C:1]([C:3]1[CH:18]=[CH:17][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[NH:19][C@H:20]1[CH2:21][CH2:22][C@H:23]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:24][CH2:25]1)#[N:2]

Participants

6

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178453999HCID 178453999, compound

Product 1

HCID 178454000HCID 178454000, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Palladium on carbon 10% by weight Degussa type (50 mg) was added to a solution of phenylmethyl 4-cyano-3-{[trans-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)cyclohexyl]amino}benzoate (71.8 mg, 0.16 mmol) in ethyl acetate (3 mL) and methanol (400 uL). The mixture was subjected to 1 atm of hydrogen for 70 min. The catalyst was then removed by filtration through celite. The resulting filtrate was concentrated to provide 4-cyano-3-{[trans-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)cyclohexyl]amino}benzoic acid (55.8 mg, 0.16 mmol) which was carried into the subsequent step without further purification. 1H NMR (400 MHz, CD3OD): 7.47 (d, 1H), 7.37 (s, 1H), 7.24 (d, 1H), 3.47-3.21 (m, 2H), 2.09 (m, 2H), 1.98 (m, 2H), 1.88 (m, 2H), 1.43 (s, 9H), 1.24 (m, 2H); MS (EI) for C19H25N3O4: 304 (MH+-tert-butyl).

Workup

  1. customThe catalyst was then removed by filtration through celite
  2. concentrationThe resulting filtrate was concentrated

Sources & evidence

ORD record
ord-016531f578724df1b609de4ff8efa68f
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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