N-(7-cyanomethyl-chroman-4-yl)-3-phenyl-3-(3-trifluoromethyl-benzenesulfonylamino)-propionamide → n-[7-(2-Aminoethyl)-chroman-4-yl]-3-phenyl-3-(3-trifluoromethylbenzenesulfonylamino)-propionamide

HRID 32094Notes

Reaction equation

HRID 32094 reaction equation
[C:1]([CH2:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]([NH:14][C:15](=[O:38])[CH2:16][CH:17]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[NH:18][S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=3)(=[O:21])=[O:20])[CH2:9][CH2:10][O:11]2)=[CH:6][CH:5]=1)#[N:2]>CO.[Pd]>[NH2:2][CH2:1][CH2:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]([NH:14][C:15](=[O:38])[CH2:16][CH:17]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[NH:18][S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:29])[F:30])[CH:23]=3)(=[O:21])=[O:20])[CH2:9][CH2:10][O:11]2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 68932619N-(7-cyanomethyl-chroman-4-yl)-3-phenyl-3-(3-trifluoromethyl-benzenesulfonylamino)-propionamide

Product 1

HCID 68929539n-[7-(2-Aminoethyl)-chroman-4-yl]-3-phenyl-3-(3-trifluoromethylbenzenesulfonylamino)-propionamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-(7-cyanomethyl-chroman-4-yl)-3-phenyl-3-(3-trifluoromethyl-benzenesulfonylamino)-propionamide (790 mg, 1.45 mmol) in MeOH (20 mL) in the Parr-bottle was added Pd/C (80 mg) while flushed under N2. The reaction mixture bottle was placed in Parr-shaker. The H2 was filled up the bottle then released-this was done 3 times. After last release, the fresh H2 (50 psi) was then filled up the bottle. The reaction was under hydrogenation for 18 h. Solvent was separated from the Pd/C by passing through the Celite®. Solvent was evaporated in vacuo to give the final product. MS m/z: 548.12 (M+H). Calc'd. for C27H28F3N3O4S-547.06.

Workup

  1. customwhile flushed under N2
  2. additionThe H2 was filled up the bottle
  3. additionAfter last release, the fresh H2 (50 psi) was then filled up the bottle
  4. customSolvent was separated from the Pd/C
  5. customSolvent was evaporated in vacuo

Sources & evidence

ORD record
ord-d04f5765686e4e7f9150a96136bcd820
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

Loading…