HCID 131734349, compound → HCID 68322480, compound

HRID 1505394Notes

Reaction equation

HRID 1505394 reaction equation
CC([N:5]([C@@H:9]([C:12]([NH:14][C:15]1[CH:16]=[N:17][C:18]([O:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[C:24]([C:30]([CH3:32])=[CH2:31])[CH:23]=2)=[CH:19][CH:20]=1)=[O:13])[CH2:10][CH3:11])[C:6](=[O:8])[O-:7])(C)C>CO.[Pd]>[C:28]([C:25]1[CH:26]=[CH:27][C:22]([O:21][C:18]2[N:17]=[CH:16][C:15]([NH:14][C:12]([C@H:9]([NH:5][C:6](=[O:8])[O:7][C:24]([CH3:30])([CH3:25])[CH3:23])[CH2:10][CH3:11])=[O:13])=[CH:20][CH:19]=2)=[CH:23][C:24]=1[CH:30]([CH3:31])[CH3:32])#[N:29]

Participants

4

Reactant 1

HCID 131734349HCID 131734349, compound2×

Product 1

HCID 68322480HCID 68322480, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1,1-dimethylethyl((1R)-1-{[(6-{[4-cyano-3-(1-methylethenyl)phenyl]oxy}-3-pyridinyl)amino]carbonyl}propyl)carbamate (Intermediate 178, 73 mg) in MeOH (10 mL) was added Pd 10% w/w on activated carbon (14 mg) and the reaction mixture was stirred for 30 minutes under H2 atmosphere (P=1 atm). The catalyst was filtered off and the solvent removed under reduced pressure. The residue was purified by flash chromatography on silica gel (SNAP 10 g) eluting from 75:25 to 40:60 cyclohexane/ethyl acetate affording the title compound (62 mg) as white solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent removed under reduced pressure
  3. customThe residue was purified by flash chromatography on silica gel (SNAP 10 g)
  4. washeluting from 75:25 to 40:60 cyclohexane/ethyl acetate affording the title compound (62 mg) as white solid

Sources & evidence

ORD record
ord-392983f0a0b3405b9ed8ab8640b91db1
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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