HCID 24954698, compound → HCID 24744045, compound

HRID 1879141Notes

Reaction equation

HRID 1879141 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]/[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:17]=2)=[N:13][C:12]=1[CH3:30])=[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][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:17]=2)=[N:13][C:12]=1[CH3:30])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 24954698HCID 24954698, compound

Product 1

HCID 24744045HCID 24744045, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-methyl-2-[6-((E)-styryl)-pyrazin-2-yl]-thiazole-5-carboxylic acid benzylamide (32 mg, 0.08 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 18 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 column chromatography [SiO2, methanol/dichloromethane, 0:100 to 5:95, v/v] and recrystallization (methanol) to afford 4-methyl-2-(6-phenethyl-pyrazin-2-yl)-thiazole-5-carboxylic acid benzylamide (18 mg, 56%). 1H NMR (400 MHz, CD2Cl2) δ 9.15 (s, 1H), 8.36 (s, 1H), 7.14-7.37 (m, 10H), 6.21 (bs, 1H), 4.60 (d, J=8.0 Hz, 2H), 3.09-3.16 (m, 4H), 2.73 (s, 3H); HRMS (M+H)+=415.16.

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 column chromatography [SiO2, methanol/dichloromethane, 0:100 to 5:95, v/v] and recrystallization (methanol)

Sources & evidence

ORD record
ord-d30d0a66b5cb4529b01206e53add57ec
Source dataset
uspto-grants-2012_11
Patent number
US08314138B2

Reaction notes

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