Trifluoroacetic acid → 2-methyl-4-(1-methyl-1H-pyrazol-4-yl)-1H-imidazol-1-amine, trifluoroacetate salt

HRID 1907186Notes

Reaction equation

HRID 1907186 reaction equation
[CH3:1][C:2]1[N:3]([NH:13]C(=O)OC(C)(C)C)[CH:4]=[C:5]([C:7]2[CH:8]=[N:9][N:10]([CH3:12])[CH:11]=2)[N:6]=1.[F:21][C:22]([F:27])([F:26])[C:23]([OH:25])=[O:24]>C(Cl)Cl>[F:21][C:22]([F:27])([F:26])[C:23]([OH:25])=[O:24].[CH3:1][C:2]1[N:3]([NH2:13])[CH:4]=[C:5]([C:7]2[CH:8]=[N:9][N:10]([CH3:12])[CH:11]=2)[N:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 123278255tert-butyl [2-methyl-4-(1-methyl-1H-pyrazol-4-yl)-1H-imidazol-1-yl]carbamate

Product 1

HCID 1317310602-methyl-4-(1-methyl-1H-pyrazol-4-yl)-1H-imidazol-1-amine, trifluoroacetate salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl [2-methyl-4-(1-methyl-1H-pyrazol-4-yl)-1H-imidazol-1-yl]carbamate (8.0 g, 29 mmol) in methylene chloride (200 mL) and trifluoroacetic acid (40 mL) was stirred at room temperature for 2.5 hours. After removal of solvents in vacuo, the residue was stirred in 1:1 ethyl acetate/heptane for 18 hours. The resulting solid was isolated by filtration to provide the product as a white solid. Yield: 5.3 g, 18 mmol, 62%. The mother liquor was concentrated in vacuo, and the residue was stirred for 30 minutes in a 1:1:1 mixture of ethyl acetate/heptane/diethyl ether (50 mL); filtration provided additional product as a white solid. Combined yield: 7.8 g, 26.8 mmol, 92%. 1H NMR (400 MHz, DMSO-d6) δ 2.54 (s, 3H), 3.89 (s, 3H), 6.55 (br s, 2H), 7.65 (s, 1H), 7.85 (d, J=0.7 Hz, 1H), 8.11 (br s, 1H).

Workup

  1. customAfter removal of solvents in vacuo
  2. customThe resulting solid was isolated by filtration

Sources & evidence

ORD record
ord-5d88696b12dc4dd3b6f7fb9a4a5af2fc
Source dataset
uspto-grants-2013_12
Patent number
US08598155B2

Reaction notes

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