HCID 66715869, compound → URB937

HRID 714014Notes

Reaction equation

HRID 714014 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:15]([O:16]CC3C=CC=CC=3)=[CH:14][CH:13]=[C:12]([O:24][C:25](=[O:33])[NH:26][CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[CH:11]=2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[NH2:2]>CCOC(C)=O.CCO.[Pd]>[C:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:15]([OH:16])=[CH:14][CH:13]=[C:12]([O:24][C:25](=[O:33])[NH:26][CH:27]3[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]3)[CH:11]=2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[NH2:2]

Participants

5

Reactant 1

HCID 66715869HCID 66715869, compound

Product 1

HCID 53394762URB937Yield 92%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of cyclohexylcarbamic acid 3′-carbamoyl-6-benzyloxybiphenyl-3-yl ester (222 mg; 0.5 mmol) in EtOAc (2.5 mL) and EtOH (2.5 mL), 10% Pd/C (22 mg) was added. The mixture was hydrogenated at 4 atm at 50° C. for 4 h, cooled, filtered on Celite and concentrated. Purification of the residue by column chromatography (cyclohexane/EtOAc 1:9) and recrystallization gave URB937 as a white solid. Yield: 92% (0.163 g). Mp: 128-130° C. (CH2Cl2/n-hexane). MS (ESI) m/z: 355.2 (M+H). 1H NMR (200 MHz, CDCl3) δ: =1.13-2.02 (m, 10H), 3.55 (m, 1H), 5.13 (br d, 1H), 5.85 (br s, 1H), 6.59 (br s, 1H), 6.74-6.95 (m, 3H), 7.07 (s, 1H), 7.34-7.41 (m, 1H), 7.56 (m, 1H), 7.68-7.75 (m, 2H) ppm. IR (Nujol) nmax: 3333, 1701, 1655 cm−1.

Workup

  1. additionwas added
  2. temperaturecooled
  3. filtrationfiltered on Celite
  4. concentrationconcentrated
  5. customPurification of the residue
  6. customby column chromatography (cyclohexane/EtOAc 1:9) and recrystallization

Sources & evidence

ORD record
ord-d3fb625f2ff54d17a16b14d8aa50c34a
Source dataset
uspto-grants-2015_11
Patent number
US09187413B2

Reaction notes

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