HCID 86606218, compound → [5-(3-Amino-phenyl)-4-methyl-thiazol-2-yl]-pyrazin-2-yl-amine

HRID 908177Notes

Reaction equation

HRID 908177 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:16][C:17]2[CH:22]=[N:21][CH:20]=[CH:19][N:18]=2)[S:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[CH:8]=1>C(OCC)(=O)C.C1COCC1.[Pd]>[NH2:13][C:9]1[CH:8]=[C:7]([C:6]2[S:5][C:4]([NH:16][C:17]3[CH:22]=[N:21][CH:20]=[CH:19][N:18]=3)=[N:3][C:2]=2[CH3:1])[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 86606218HCID 86606218, compound

Product 1

HCID 85996839[5-(3-Amino-phenyl)-4-methyl-thiazol-2-yl]-pyrazin-2-yl-amineYield 36.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21939870Tetrahydrofuran ethyl acetateSolvent

Procedure

[4-Methyl-5-(3-nitro-phenyl)-thiazol-2-yl]-pyrazin-2-yl-amine (42b) (1.079 g, 3.4 mmol) is dissolved in ethyl acetate/THF (5/1, 240 ml) and stirred at room temperature under an atmosphere of argon. The solution is then treated with 10% Pd/C (1.1 g). The reaction mixture is purged three times with nitrogen and placed under an atmosphere of hydrogen overnight. The mixture is then filtered through celite and the catalyst is washed with THF (200 ml). The solvent is removed in vacuo to leave [5-(3-amino-phenyl)-4-methyl-thiazol-2-yl]-pyrazin-2-yl-amine (0.351 g, 36%). MH+ (ESMS):283.5

Workup

  1. customThe reaction mixture is purged three times with nitrogen
  2. filtrationThe mixture is then filtered through celite
  3. washthe catalyst is washed with THF (200 ml)
  4. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-6a77bf69462244618ba2e7859c6a5f65
Source dataset
uspto-grants-2011_09
Patent number
US08017608B2

Reaction notes

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