Hydrochloric Acid → HCID 58683727, compound

HRID 1991058Notes

Reaction equation

HRID 1991058 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1/[CH:16]=[CH:17]/[C:18]([OH:20])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.Cl.Cl.[F:34][C:35]1[CH:48]=[CH:47][C:38]([CH2:39][N:40]2[CH2:45][CH2:44][NH:43][CH:42]([CH3:46])[CH2:41]2)=[CH:37][CH:36]=1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1/[CH:16]=[CH:17]/[C:18]([N:43]1[CH2:44][CH2:45][N:40]([CH2:39][C:38]2[CH:47]=[CH:48][C:35]([F:34])=[CH:36][CH:37]=2)[CH2:41][CH:42]1[CH3:46])=[O:20])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 107035841-(4-Fluorobenzyl)-3-methylpiperazineHCID 58683732HCID 58683732, compound

Product 1

HCID 58683727HCID 58683727, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(E)-3-(2-tert-Butyloxycarbonylamino-5chlorophenyl)-acrylic acid (1.0 g, 3.36 mmol) and EDCl.HCl (645 mg, 3.36 mmol) and racemic 1-(4-fluorobenzyl)-3-methyl-piperazine (Bolos, Jordi et al. J. Med. Chem. (1996), 39(15), 2962-2970) (770 mg, 3.7 mmol) were dissolved in CH2Cl2 (34 ml) and stirred at room temperature for 4 hours. The reaction mixture was purified via chromatography (SiO2, EtOAc/hexanes 1/1) to yield the title compound as colorless foam (1.2 g, 74%).

Workup

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

Sources & evidence

ORD record
ord-560a3fe57ec64e0bac1e53e315c1bb39
Source dataset
uspto-grants-2010_01
Patent number
US07645760B2

Reaction notes

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