Hydrochloric Acid → (4-Bromo-1-methyl-1H-pyrazol-3-yl)-1-piperazinylmethanone

HRID 56353Notes

Reaction equation

HRID 56353 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:20]([Br:21])=[CH:19][N:18]([CH3:22])[N:17]=2)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[Br:21][C:20]1[C:16]([C:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[O:15])=[N:17][N:18]([CH3:22])[CH:19]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 46901911tert-Butyl 4-(4-bromo-1-methyl-1H-pyrazole-3-carbonyl)piperazine-1-carboxylate

Product 1

HCID 46901601(4-Bromo-1-methyl-1H-pyrazol-3-yl)-1-piperazinylmethanoneYield 100.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-(4-Bromo-1-methyl-1H-pyrazole-3-carbonyl)-piperazine-1-carboxylic acid tert-butyl ester (800 mg, 2.14 mmol) from Step A and HCl in dioxane (4 N, 5.36 mL) was stirred at room temperature for 1 h. The solvent was removed under reduced pressure to afford the hydrochloride salt of the title compound (585 mg) as a light yellow solid. 1H NMR (Acetonitrile-d3, 400 MHz) δ 3.20-3.26 (m, 4H), 3.92 (s, 3H), 3.98-4.05 (m, 4H), 7.71 (s, 1H), 9.40-9.50 (bs, 2H). Exact mass calculated for C9H13BrN4O: 272.0. Found: LCMS m/z (%)=273.0 (M+H+79Br, 100%), 275.0 (M+H+81Br, 97%).

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-32fc4f4a57054be688c901f51cc62f2f
Source dataset
uspto-grants-2016_09
Patent number
US09434692B2

Reaction notes

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