HCID 68489051, compound → 4-Methyl-2-[5-(3-phenyl-propyl)-pyrazin-2-yl]-thiazole-5-carboxylic acid benzylamide

HRID 1879152Notes

Reaction equation

HRID 1879152 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([C:16]2[CH:21]=[N:20][C:19](/[CH:22]=[CH:23]/[CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:18][N:17]=2)=[N:13][C:12]=1[CH3:31])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OCC)(=O)C.[Pd]>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([C:16]2[CH:21]=[N:20][C:19]([CH2:22][CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:18][N:17]=2)=[N:13][C:12]=1[CH3:31])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 68489051HCID 68489051, compound

Product 1

HCID 249543254-Methyl-2-[5-(3-phenyl-propyl)-pyrazin-2-yl]-thiazole-5-carboxylic acid benzylamideYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Part B. To a solution of 4-methyl-2-[5-((E)-3-phenyl-propenyl)-pyrazin-2-yl]-thiazole-5-carboxylic acid benzylamide (20 mg, 0.05 mmol, 1.0 equiv) in ethyl acetate was added Pd/C (15 mg, 10%). The flask was first purged with nitrogen, then with hydrogen. The reaction mixture was stirred at ambient temperature for 60 hr and monitored by LCMS. Upon completion, the reaction mixture was diluted with ethyl acetate, filtered through Celite and concentrated in vacuo. The crude product was purified by preparative HPLC (acetonitrile/water, 0.1% trifluoroacetic acid) to afford 4-methyl-2-[5-(3-phenyl-propyl)-pyrazin-2-yl]-thiazole-5-carboxylic acid benzylamide (12 mg, 60%). 1H NMR (400 MHz, CD2Cl2) δ 9.25 (s, 1H), 8.38 (s, 1H), 7.14-7.35 (m, 10H), 6.20 (bs, 1H), 4.58 (d, J=4.0 Hz, 2H), 2.87 (t, J=8.0 Hz, 2H), 2.72 (s, 3H), 2.69 (t, J=8.0 Hz, 2H), 2.07-2.13 (m, 2H); HRMS (M+H)+=429.17.

Workup

  1. customThe flask was first purged with nitrogen
  2. additionUpon completion, the reaction mixture was diluted with ethyl acetate
  3. filtrationfiltered through Celite
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by preparative HPLC (acetonitrile/water, 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-4b24692b98d54eb2aac0244868e548f9
Source dataset
uspto-grants-2012_11
Patent number
US08314138B2

Reaction notes

Loading…