2-[1-Methyl-3-(trifluoromethyl)pyrazol-5-yl]-5-nitro-1,3-thiazole → 5-Amino-2-[1-methyl-3-(trifluoromethyl)pyrazol-5-yl]-1,3-thiazole

HRID 1524246Notes

Reaction equation

HRID 1524246 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[S:8][C:9]([N+:12]([O-])=O)=[CH:10][N:11]=2)=[CH:5][C:4]([C:15]([F:18])([F:17])[F:16])=[N:3]1>CO.[Pd]>[NH2:12][C:9]1[S:8][C:7]([C:6]2[N:2]([CH3:1])[N:3]=[C:4]([C:15]([F:18])([F:17])[F:16])[CH:5]=2)=[N:11][CH:10]=1

Participants

4

Reactant 1

HCID 667801512-[1-Methyl-3-(trifluoromethyl)pyrazol-5-yl]-5-nitro-1,3-thiazole

Product 1

HCID 667789175-Amino-2-[1-methyl-3-(trifluoromethyl)pyrazol-5-yl]-1,3-thiazoleYield 25.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-[1-methyl-3-(trifluoromethyl)pyrazol-5-yl]-5-nitro-1,3-thiazole (65, 350 mg, 0.13 mmol) and Pd/C in 4 ml MeOH was stirred under H2 balloon at r.t. for 4 h before filtered thru celite. The filtrate was concentrated to dryness to give 8.1 mg 5-amino-2-[1-methyl-3-(trifluoromethyl)pyrazol-5-yl]-1,3-thiazole (66) as brown thick oil which was used directly used for next step reaction.

Workup

  1. filtrationbefore filtered thru celite
  2. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-8e4dc340667941ed9b715aefcbbbe87e
Source dataset
uspto-grants-2015_07
Patent number
US09079891B2

Reaction notes

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