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Indole-3-pyruvic acid → N-cyclohexyl 3-indolepyruvamide

HRID 359727
Notes
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Reaction equation

HRID 359727 reaction equation
C[N-]C.[NH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH2:13][C:14](=[O:18])[C:15]([OH:17])=O)=[CH:5]1.[CH:19]1[CH:20]=[CH:21][C:22]2N(O)N=[N:25][C:23]=2[CH:24]=1.C1(N)CCCCC1.CN1CCOCC1>CCN=C=NCCCN(C)C.Cl>[CH:23]1([NH:25][C:15](=[O:17])[C:14]([CH2:13][C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[NH:4][CH:5]=2)=[O:18])[CH2:24][CH2:19][CH2:20][CH2:21][CH2:22]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 803Indole-3-pyruvic acidHCID 7965CyclohexylamineHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 182180Dimethylazanide

Product 1

HCID 54134943N-cyclohexyl 3-indolepyruvamide

Reagents, catalysts & solvents 1

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideSolvent

Procedure

The same method as described in Example 7 was followed for the preparation of N,N-dimethylamide. 500 mg 3-indolepyruvic acid were reacted with 400 ml HOBt and 570 ml EDC.HCl. 340 microliters of freshly distilled cyclohexylamine and 325 microliters NMM were added to the solution, which was reacted for 5 hours.

Workup

  1. customwas reacted for 5 hours

Sources & evidence

ORD record
ord-ab4f0216453f46f89472cb195305881f
Source dataset
uspto-grants-1991_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05002963

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes