Hydrochloric Acid → (5-Chloro-2-[(E)-3-[-4-(4-fluorobenzyl)-piperazin-1-yl]-3-oxopropenyl]-phenyl)-carbamic acid tert butyl ester

HRID 1991051Notes

Reaction equation

HRID 1991051 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1/[CH:16]=[CH:17]/[C:18]([OH:20])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:21][C:22]1[CH:34]=[CH:33][C:25]([CH2:26][N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[CH:24][CH:23]=1.CCN=C=NCCCN(C)C.Cl.Cl>C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1/[CH:16]=[CH:17]/[C:18]([N:30]1[CH2:29][CH2:28][N:27]([CH2:26][C:25]2[CH:33]=[CH:34][C:22]([F:21])=[CH:23][CH:24]=2)[CH2:32][CH2:31]1)=[O:20])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7965631-(4-Fluorobenzyl)piperazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 116307753-(2-{[(Tert-butoxy)carbonyl]amino}-4-chlorophenyl)prop-2-enoic acid

Product 1

HCID 58683691(5-Chloro-2-[(E)-3-[-4-(4-fluorobenzyl)-piperazin-1-yl]-3-oxopropenyl]-phenyl)-carbamic acid tert butyl esterYield 63.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(E)-3-(2-tert-Butoxycarbonylamino-4-chlorophenyl)-acrylic acid (150 mg, 0.5 mmol), 1-(4-fluorobenzyl)-piperazine (98 mg, 0.5 mmol) and EDCl.HCl (96 mg, 0.5 mmol) were dissolved in CH2Cl2 and stirred at room temperature for 18 hours. The reaction mixture was purified via chromatography (SiO2, EtOAc) to yield the title compound as a white foam (150 mg, 63%).

Workup

  1. customThe reaction mixture was purified via chromatography (SiO2, EtOAc)

Sources & evidence

ORD record
ord-3a4be4e2c0ad488ab6c04b0598a1cd6d
Source dataset
uspto-grants-2010_01
Patent number
US07645760B2

Reaction notes

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