HCID 24954329, compound → 4-Methyl-2-{6-[2-(4-trifluoromethyl-phenyl)-ethyl]-pyrazin-2-yl}-thiazole-5-carboxylic acid benzylamide

HRID 1879147Notes

Reaction equation

HRID 1879147 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][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=3)[N:17]=2)=[N:13][C:12]=1[CH3:34])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OCC)(=O)C.C(O)C.[OH-].[OH-].[Pd+2]>[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:25]=[CH:26][C:27]([C:30]([F:31])([F:33])[F:32])=[CH:28][CH:29]=3)[N:17]=2)=[N:13][C:12]=1[CH3:34])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 24954329HCID 24954329, compound

Product 1

HCID 249547004-Methyl-2-{6-[2-(4-trifluoromethyl-phenyl)-ethyl]-pyrazin-2-yl}-thiazole-5-carboxylic acid benzylamideYield 51.8%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

To a solution of 4-methyl-2-{6-[(E)-2-(4-trifluoromethyl-phenyl)-vinyl]-pyrazin-2-yl}-thiazole-5-carboxylic acid benzylamide (40 mg, 0.08 mmol, 1.0 equiv) in ethyl acetate/ethanol (1:1) was added Pd(OH)2 (10 mg, 20%). The flask was first purged with nitrogen, then with hydrogen. The reaction mixture was stirred at ambient temperature for 3 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-{6-[2-(4-trifluoromethyl-phenyl)-ethyl]-pyrazin-2-yl}-thiazole-5-carboxylic acid benzylamide (20 mg, 50%). 1H NMR (400 MHz, CD2Cl2) δ 9.16 (s, 1H), 8.39 (s, 1H), 7.52 (d, J=8.0 Hz, 2H), 7.28-7.37 (m, 7H), 6.25 (bs, 1H), 4.60 (d, J=8.0 Hz, 2H), 3.19 (apparent s, 4H), 2.72 (s, 3H); HRMS (M+H)+=483.14.

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-d6eb9165629b498d98227f2d982a37b6
Source dataset
uspto-grants-2012_11
Patent number
US08314138B2

Reaction notes

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