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Triethylamine → N-methyl-N-[2-(1,3-thiazol-2-yl)-1H-indol-7-yl]pyrrolidine-1-carboxamide

HRID 1851593
Notes
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Reaction equation

HRID 1851593 reaction equation
Cl.[CH3:2][NH:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]1[S:14][CH:15]=[CH:16][N:17]=1)=[CH:9]2.C(N(CC)CC)C.[N:25]1([C:30](Cl)=[O:31])[CH2:29][CH2:28][CH2:27][CH2:26]1.C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:2][N:3]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]1[S:14][CH:15]=[CH:16][N:17]=1)=[CH:9]2)[C:30]([N:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1)=[O:31]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 709371-Pyrrolidinecarbonyl chlorideHCID 516892Sodium BicarbonateHCID 67109280N-Methyl-2-(1,3-thiazol-2-yl)-1H-indole-7-amine hydrochloride

Product 1

HCID 11978714N-methyl-N-[2-(1,3-thiazol-2-yl)-1H-indol-7-yl]pyrrolidine-1-carboxamideYield 5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-methyl-2-(1,3-thiazol-2-yl)-1H-indole-7-amine hydrochloride (133 mg) and triethylamine (105 μL) in tetrahydrofuran (5 mL) was added pyrrolidine-1-carbonylchloride (100 mg). The reaction mixture was stirred at room temperature for 1 hr. Saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:1) to give yellow crystals (8.2 mg, yield 5%). melting point 182° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6547fd8a27ba4a2d95ccc809ea01ee94
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08957070B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes