Cyclopropylamine → HCID 54720418, compound

HRID 2364174Notes

Reaction equation

HRID 2364174 reaction equation
[CH2:1]([C:8]1[CH:17]=[C:16]2[C:11]([C:12]([OH:31])=[C:13]([C:26]([O:28]CC)=O)[C:14](=[O:25])[N:15]2[CH2:18][C:19]2[N:20]([CH3:24])[CH:21]=[CH:22][N:23]=2)=[N:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:32]1([NH2:35])[CH2:34][CH2:33]1>>[CH2:1]([C:8]1[CH:17]=[C:16]2[C:11]([C:12]([OH:31])=[C:13]([C:26]([NH:35][CH:32]3[CH2:34][CH2:33]3)=[O:28])[C:14](=[O:25])[N:15]2[CH2:18][C:19]2[N:20]([CH3:24])[CH:21]=[CH:22][N:23]=2)=[N:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 69828CyclopropylamineHCID 58882914HCID 58882914, compound

Product 1

HCID 54720418HCID 54720418, compound

Procedure

This compound was prepared from ethyl 7-benzyl-4-hydroxy-1-[(1-methyl-1H-imidazol-2-yl)methyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and cyclopropylamine using methods similar to those described in Example 11. The product was obtained as a white solid: 1H NMR (CDCl3) δ 10.02 (1H, br), 8.57 (1H, s), 8.45 (1H, br s), 7.30-7.21 (5H, m), 7.01 (1H, br s), 6.83 (1H, s), 5.69 (2H, br), 4.17 (2H, s), 3.67 (3H, s), 2.95 (1H, m), 0.91 (2H, m), 0.71 (2H, m); HRMS calcd for C24H23N5O3+H+: 430.1879. Found: 430.1877.

Workup

  1. customThe product was obtained as a white solid

Sources & evidence

ORD record
ord-f1c4609aa4e4440089c430976bf2d83a
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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