Trifluoroacetic acid → 4-(5-bromo-1-methyl-1H-pyrazol-4-yl)-2-methyl-1H-imidazol-1-amine, trifluoroacetate salt

HRID 1498026Notes

Reaction equation

HRID 1498026 reaction equation
C(OC(=O)[NH:7][N:8]1[CH:12]=[C:11]([C:13]2[CH:14]=[N:15][N:16]([CH3:19])[C:17]=2[Br:18])[N:10]=[C:9]1[CH3:20])(C)(C)C.[F:22][C:23]([F:28])([F:27])[C:24]([OH:26])=[O:25]>ClCCl>[F:22][C:23]([F:28])([F:27])[C:24]([OH:26])=[O:25].[Br:18][C:17]1[N:16]([CH3:19])[N:15]=[CH:14][C:13]=1[C:11]1[N:10]=[C:9]([CH3:20])[N:8]([NH2:7])[CH:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86669718tert-butyl [4-(5-bromo-1-methyl-1H-pyrazol-4-yl)-2-methyl-1H-imidazol-1-yl]carbamate

Product 1

HCID 1317310614-(5-bromo-1-methyl-1H-pyrazol-4-yl)-2-methyl-1H-imidazol-1-amine, trifluoroacetate salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl[4-(5-bromo-1-methyl-1H-pyrazol-4-yl)-2-methyl-1H-imidazol-1-yl]carbamate (5.00 g, 14.0 mmol) was dissolved in dichloromethane (120 mL), treated with trifluoroacetic acid (20.9 mL, 281 mmol), and stirred for 2.5 hours. After removal of volatiles in vacuo, the oily residue was diluted with diethyl ether (100 mL). The resulting suspension was stirred for 30 minutes at room temperature, and then the solid was collected and washed with diethyl ether to provide the product as an off-white solid. Yield: 4.98 g, 13.5 mmol, 96%. LCMS m/z 256.3 (M+1). 1H NMR (500 MHz, CD3OD) δ 2.65 (s, 3H), 3.95 (s, 3H), 7.68 (s, 1H), 7.86 (s, 1H).

Workup

  1. customAfter removal of volatiles in vacuo
  2. additionthe oily residue was diluted with diethyl ether (100 mL)
  3. stirringThe resulting suspension was stirred for 30 minutes at room temperature
  4. customthe solid was collected
  5. washwashed with diethyl ether

Sources & evidence

ORD record
ord-1a8a9034cabc41bb86c1c67b8ee160ea
Source dataset
uspto-grants-2015_12
Patent number
US09200000B2

Reaction notes

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