Pyrrole-2-Carboxylic Acid → HCID 15392050, compound

HRID 361797Notes

Reaction equation

HRID 361797 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:25][CH3:26])[C:15]2[C:20]([CH:21]=[C:22]([CH3:24])[CH3:23])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[NH:39]1[CH:43]=[CH:42][CH:41]=[C:40]1[C:44]([OH:46])=O>[OH-].[OH-].[Pd+2]>[NH:39]1[CH:43]=[CH:42][CH:41]=[C:40]1[C:44]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:25][CH3:26])[C:15]2[C:20]([CH2:21][CH:22]([CH3:23])[CH3:24])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=[O:46]

Participants

5

Reactant 3

HCID 12473Pyrrole-2-Carboxylic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 106654941-Benzyl-4-[N-ethyl-N-(3-(2-methyl-1-propenyl)-2-pyridinyl)amino]piperidine

Product 1

HCID 15392050HCID 15392050, compound

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideCatalyst

Procedure

Following the general procedure of EXAMPLE 20 and making non-critical variations but starting with 1-benzyl-4-[N-ethyl-N-(3-(2-methyl-1-propenyl)-2-pyridinyl)amino]piperidine (XXII, EXAMPLE 17, 0.67 g, 1.92 mmol), Pearlman's catalyst (0.1 g), CDI (0.31 g, 1.92 mmol) and pyrrole-2-carboxylic acid (0.213 g, 1.92 mmol), the title compound is obtained, HRMS Calcd. for C21H30N4O=354.2419, found=354.2413.

Sources & evidence

ORD record
ord-24695953d3f94df9b681d0f94397a880
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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