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Triethylamine → HCID 12074886, compound

HRID 1455673
Notes
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Reaction equation

HRID 1455673 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:16])[N:5]([CH2:12][C:13]([OH:15])=O)[C:6]2=[O:11].[N:17]1([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>ClCCl>[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:16])[N:5]([CH2:12][C:13]([N:20]1[CH2:19][CH2:18][N:17]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:22][CH2:21]1)=[O:15])[C:6]2=[O:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 8297952-(4-Amino-1,3-dioxoisoindolin-2-yl)acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 12074886
HCID 12074886, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2 g (9.08 mmol) of (4-amino-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetic acid, 1.692 g (9.08 mmol) of tert-butyl 1-piperazinecarboxylate, 1.916 g (10 mmol) of N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride, 1.35 g (10 mmol) of 1-hydroxy-1H-benzotriazole and 3.8 ml (27 mmol) of triethylamine are stirred in 200 ml of dichloromethane at RT overnight. The reaction mixture is then washed with sat. aqu. NaHCO3 solution, dried over MgSO4, filtered and concentrated. The crude product (3.05 g) can be used without further purification for the next step or, if required, be chromatographed on silica gel (CH2Cl2/EtOH=1/0 to 2/1+0.1% conc. aqueous ammonia solution) for purification.

Workup

  1. washThe reaction mixture is then washed with sat. aqu
  2. dry with materialNaHCO3 solution, dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product (3.05 g) can be used without further purification for the next step
  6. custombe chromatographed on silica gel (CH2Cl2/EtOH=1/0 to 2/1+0.1% conc. aqueous ammonia solution) for purification

Sources & evidence

ORD record
ord-bb90287aa8724306a13e98650b8f7a52
Source dataset
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07482472B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes