4-methyl-2-[6-((E)-3-phenyl-propenyl)-pyrazin-2-yl]-thiazole-5-carboxylic acid benzylamide → 4-Methyl-2-[6-(3-phenyl-propyl)-pyrazin-2-yl]-thiazole-5-carboxylic acid benzylamide

HRID 1879143Notes

Reaction equation

HRID 1879143 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([C:16]2[CH:21]=[N:20][CH:19]=[C:18](/[CH:22]=[CH:23]/[CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[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][CH:19]=[C:18]([CH2:22][CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[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 684877744-methyl-2-[6-((E)-3-phenyl-propenyl)-pyrazin-2-yl]-thiazole-5-carboxylic acid benzylamide

Product 1

HCID 594895384-Methyl-2-[6-(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-[6-((E)-3-phenyl-propenyl)-pyrazin-2-yl]-thiazole-5-carboxylic acid benzylamide (39 mg, 0.09 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 prep HPLC (acetonitrile/water, 0.1% trifluoroacetic acid) to afford 4-methyl-2-[6-(3-phenyl-propyl)-pyrazin-2-yl]-thiazole-5-carboxylic acid benzylamide (19 mg, 60%). 1H NMR (400 MHz, CD2Cl2) δ 9.14 (s, 1H), 9.12 (s, 1H), 7.14-7.36 (m, 10H), 6.23 (bs, 1H), 4.59 (d, J=8.0 Hz, 2H), 2.86 (t, J=8.0 Hz, 2H), 2.72 (s, 3H), 2.69-2.72 (m, 2H), 2.07-2.15 (m, 21-1); 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 prep HPLC (acetonitrile/water, 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-d6d880feda7743e6b97565f51db3612d
Source dataset
uspto-grants-2012_11
Patent number
US08314138B2

Reaction notes

Loading…