1-Hydroxybenzotriazole → HCID 59559647, compound

HRID 1178147Notes

Reaction equation

HRID 1178147 reaction equation
C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[Br:20][C:21]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:22]=1[C:23]([OH:25])=O.CCN=C=NCCCN(C)C.Cl.[C:44]([O:48][C:49](=[O:60])[NH:50][CH2:51][C:52](=[O:59])[N:53]1[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1)([CH3:47])([CH3:46])[CH3:45]>CN(C=O)C.O>[C:44]([O:48][C:49](=[O:60])[NH:50][CH2:51][C:52]([N:53]1[CH2:54][CH2:55][N:56]([C:23](=[O:25])[C:22]2[CH:26]=[C:27]([O:30][CH3:31])[CH:28]=[CH:29][C:21]=2[Br:20])[CH2:57][CH2:58]1)=[O:59])([CH3:47])([CH3:45])[CH3:46]

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 899062-Bromo-5-methoxybenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 17750349tert-butyl N-(2-oxo-2-(piperazin-1-yl)ethyl)carbamate

Product 1

HCID 59559647HCID 59559647, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

HOBt (125 mg, 0.93 mmol) and DIPEA (287 mg, 2.2 mmol) were added to a stirred solution of 2-bromo-5-methoxy-benzoic acid (171 mg, 0.74 mmol) in DMF (2.5 mL). The mixture was then cooled to 10° C. and EDCI.HCl (178 mg, 0.93 mmol) followed by (2-oxo-2-piperazin-1-yl-ethyl)-carbamic acid tert-butyl ester (200 mg, 0.82 mmol) were added. The reaction mixture was then stirred at room temperature overnight. Water was added, and the product was extracted with ethyl acetate. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated. Purification using column chromatography (silica gel (60-120 mesh) and 50% ethyl acetate in hexane as the eluent) afforded {2-[4-(2-Bromo-5-methoxy-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester in 97% yield. LC-MS purity: 97.79%

Workup

  1. additionwere added
  2. extractionthe product was extracted with ethyl acetate
  3. washThe organic layer was washed with brine solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification

Sources & evidence

ORD record
ord-a87f2c2a13cc4088aca624ab48537efd
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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