N-Cyclopropylbenzenemethanamine → Ethyl 2-[({4-[benzyl(cyclopropyl)amino]butyl}[(tert-butoxy)carbonyl]amino)methyl]pyridine-4-carboxylate

HRID 1507149Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]([CH2:14][C:15]1[CH:20]=[C:19]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:18]=[CH:17][N:16]=1)[CH2:9][CH2:10][CH2:11][CH:12]=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:26]([NH:33][CH:34]1[CH2:36][CH2:35]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[CH2:26]([N:33]([CH:34]1[CH2:35][CH2:36]1)[CH2:12][CH2:11][CH2:10][CH2:9][N:8]([CH2:14][C:15]1[CH:20]=[C:19]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:18]=[CH:17][N:16]=1)[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

Reactant 2

HCID 25866N-Cyclopropylbenzenemethanamine

HCID 90375049HCID 90375049, compound

Product 1

HCID 90374996Ethyl 2-[({4-[benzyl(cyclopropyl)amino]butyl}[(tert-butoxy)carbonyl]amino)methyl]pyridine-4-carboxylate

Procedure

By General Procedure A from ethyl 2-({[(tert-butoxy)carbonyl](4-oxobutyl)amino}methyl)pyridine-4-carboxylate and N-benzylcyclopropanamine. Purification by column chromatography (5% MeOH/DCM) gave the title compound as colorless oil. 1H-NMR (300 MHz, CDCl3): δ 8.60 (d, 1H), 7.70 (s, 1H), 7.60 (d, 1H), 7.10 (m, 5H), 4.50 (d, 2H), 4.40 (q, 2H), 3.50 (m, 2H), 3.15 (m, 2H), 2.50 (m, 2H), 1.60 (m, 1H), 1.45 (m, 16H), 0.4 (m, 4H) ppm.

Workup

customPurification by column chromatography (5% MeOH/DCM)

Sources & evidence

ORD record: ord-46c19ee01a5d48468ac85906a920ba04
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221801B2

Reaction notes

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