1-(Cyclobutylmethyl)piperazine → 5-Bromo-4-(4-(cyclobutylmethyl)piperazin-1-yl)-3-nitropyridin-2-amine

HRID 416895Notes

Reaction equation

HRID 416895 reaction equation
[CH:1]1([CH2:5][N:6]2[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[CH2:4][CH2:3][CH2:2]1.[Br:12][C:13]1[C:14](Cl)=[C:15]([N+:20]([O-:22])=[O:21])[C:16]([NH2:19])=[N:17][CH:18]=1>CC(O)C.CCN(C(C)C)C(C)C>[Br:12][C:13]1[C:14]([N:9]2[CH2:8][CH2:7][N:6]([CH2:5][CH:1]3[CH2:2][CH2:3][CH2:4]3)[CH2:11][CH2:10]2)=[C:15]([N+:20]([O-:22])=[O:21])[C:16]([NH2:19])=[N:17][CH:18]=1

Participants

5

Reactant 2

HCID 9523181-(Cyclobutylmethyl)piperazineHCID 454802365-Bromo-4-chloro-3-nitropyridin-2-amine

Product 1

HCID 578972675-Bromo-4-(4-(cyclobutylmethyl)piperazin-1-yl)-3-nitropyridin-2-amineYield 45%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
60 °C

Procedure

The resulting 1-(cyclobutylmethyl)piperazine (supposedly 0.086 g, 0.56 mmol, 1 eq) was suspended in iPrOH (0.55 mL) and DIPEA (0.22 mL). To this solution, 5-bromo-4-chloro-3-nitropyridin-2-amine (0.14 g, 0.56 mmol, 1 eq) was added and the reaction mixture was heated and stirred for 17 h at 60° C. The mixture was filtered, washed with iPrOH (3×3 mL), Et2O (2×3 mL), and dried to give the title compound as a bright yellow powder (0.093 g, 45%); 1H-NMR (500 MHz, DMSO-d6): δ 1.73-1.92 (m, 2H), 1.96-2.05 (m, 2H), 2.37 (d, J=7.0 Hz, 2H, piperazine N(CH2)2), 2.41-2.54 (m, 5H), 3.02 (m, 4H), 6.95 (s, 2H, NH2), 8.15 (s, 1H, pyridine 6-H); LC (Method B)-MS (ESI, m/z): Rt=2.02 min—370/372 [(M+H+), Br isotopic pattern, 100%].

Workup

  1. temperaturethe reaction mixture was heated
  2. filtrationThe mixture was filtered
  3. washwashed with iPrOH (3×3 mL), Et2O (2×3 mL)
  4. customdried

Sources & evidence

ORD record
ord-a937997163404cc6aebdf5e73b4f5129
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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