1-Hydroxybenzotriazole → HCID 66621478, compound

HRID 415314Notes

Reaction equation

HRID 415314 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=O)=[O:4].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[CH:36]1([C:39]([N:41]2[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]2)=[O:40])[CH2:38][CH2:37]1>ClCCl.O.C(N(CC)CC)C>[CH:36]1([C:39]([N:41]2[CH2:46][CH2:45][N:44]([C:8]([C:7]3[CH:6]=[C:5]([CH:13]=[CH:12][CH:11]=3)[C:3]([O:2][CH3:1])=[O:4])=[O:10])[CH2:43][CH2:42]2)=[O:40])[CH2:37][CH2:38]1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 6018803-(Methoxycarbonyl)benzoic acidHCID 20642351-(Cyclopropylcarbonyl)piperazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 66621478HCID 66621478, compoundYield 60.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 3-(methoxycarbonyl)benzoic acid (0.9 g, 5 mmol) in dichloromethane (20 mL), 1-hydroxybenzotriazole (0.75 g, 5.5 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.06 g, 5.5 mmol) and triethyl amine (2 mL) were added. The mixture was stirred at room temperature for 30 min, and then cyclopropyl(piperazin-1-yl)methanone (1.0 g, 5 mmol) was added and the mixture was stirred at room temperature for 16 h. The resulting mixture was added water (50 mL) and extracted with dichloromethane (100 mL×3), the organic phase was washed with sodium bicarbonate, brine and concentrated. The crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate 20:1 to 2:1), 0.95 g of methyl 3-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl)benzoate as an oil was obtained, Yield 60%. 1H-NMR (400 MHz, CDCl3) 0.80-0.82 (m, 2H), 1.00-1.04 (m, 2H), 1.24-1.27 (m, 1H), 3.25-3.78 (m, 8H), 3.94 (s, 3H), 7.52-7.55 (t, J=7.6 Hz, 1H), 7.63-7.65 (d, J=7.6 Hz, 1H), 8.09-8.14 (m, 2H); LC-MS (ESI) m/z: 317 (M+1)+.

Workup

  1. stirringthe mixture was stirred at room temperature for 16 h
  2. extractionextracted with dichloromethane (100 mL×3)
  3. washthe organic phase was washed with sodium bicarbonate, brine
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate 20:1 to 2:1)

Sources & evidence

ORD record
ord-6ee3b808430c4cb986c96b78c5a56746
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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