Triethylamine → HCID 89770796, compound

HRID 1519561Notes

Reaction equation

HRID 1519561 reaction equation
Cl.[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C@H:12]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[C:13]([O:15][CH3:16])=[O:14])=[CH:7][CH:6]=1)([O-:4])=[O:3].Br[CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=1.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C@H:12]([N:17]2[CH2:18][CH2:19][N:20]([CH2:24][CH2:25][C:26]3[CH:27]=[CH:28][C:29]([N+:32]([O-:34])=[O:33])=[CH:30][CH:31]=3)[CH2:21][CH2:22]2)[C:13]([O:15][CH3:16])=[O:14])=[CH:7][CH:6]=1)([O-:4])=[O:3]

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 792664-Nitrophenethyl bromide2×HCID 118202440HCID 118202440, compound

Product 1

HCID 89770796HCID 89770796, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl(2S)-3-(4-nitrophenyl)-2-piperazin-1-ylpropanoate hydrochloride (100 mg, 0.30 mmol), 1-(2-bromoethyl)-4-nitrobenzene (77 mg, 0.33 mmol), and triethylamine (92 mg, 0.91 mmol) in DMF was heated to 60° C. for 16 hours. LC showed some product. More 1-(2-bromoethyl)-4-nitrobenzene (77 mg, 0.33 mmol) and triethylamine (92 mg, 0.91 mmol) were added to the reaction, and the mixture was allowed to heat for another 24 hours. LC showed complete reaction at that point. The reaction was diluted with EtOAc, washed with water, and purified by HPLC to deliver the desired product. LC-MS (IE, m/z): 443 [M+1]+. (0.51 μM)

Workup

  1. temperatureto heat for another 24 hours
  2. customreaction at that point
  3. washwashed with water
  4. custompurified by HPLC

Sources & evidence

ORD record
ord-9a9b061b1d9446b797043ebd94a730d9
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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