Hydrochloric Acid → HCID 58683712, compound

HRID 1991049Notes

Reaction equation

HRID 1991049 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:36]=[CH:35][C:25]([CH2:26][N:27]2[CH2:32][C@@H:31]([CH3:33])[NH:30][CH2:29][C@@H:28]2[CH3:34])=[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][C@H:28]([CH3:34])[N:27]([CH2:26][C:25]2[CH:35]=[CH:36][C:22]([F:21])=[CH:23][CH:24]=2)[CH2:32][C@H:31]1[CH3:33])=[O:20])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 116307753-(2-{[(Tert-butoxy)carbonyl]amino}-4-chlorophenyl)prop-2-enoic acidHCID 12112118(2S,5R)-1-(4-Fluorobenzyl)-2,5-dimethylpiperazine

Product 1

HCID 58683712HCID 58683712, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(E)-3-(2-tert-Butoxycarbonylamino-4-chlorophenyl)-acrylic acid (595 mg, 2.0 mmol) and (2S,5R)-1-(4-fluorobenzyl)-2,5-dimethylpiperazine (Mavunkel, Babu J. et al., WO 00/71535) (445 mg, 2.0 mmol) were dissolved in CH2Cl2, combined with EDCl.HCl (384 mg, 2.0 mmol) and stirred for 3 hours at room temperature. The reaction mixture was purified via chromatography (SiO2, EtOAc/hexanes 2/8) to yield the title compound as colorless foam (830 mg, 81%).

Workup

  1. customThe reaction mixture was purified via chromatography (SiO2, EtOAc/hexanes 2/8)

Sources & evidence

ORD record
ord-3a4fcf0d26ff41d5a64652268a2dfe49
Source dataset
uspto-grants-2010_01
Patent number
US07645760B2

Reaction notes

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