Cyclopropylamine → HCID 54706894, compound

HRID 2364156Notes

Reaction equation

HRID 2364156 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:9][N:10]=2)[NH:5][C:4](=[O:19])[C:3]=1[C:20]([O:22]CC)=O.[CH:25]1([NH2:28])[CH2:27][CH2:26]1>CC(N(C)C)=O>[CH:25]1([NH:28][C:20]([C:3]2[C:4](=[O:19])[NH:5][C:6]3[C:11]([C:2]=2[OH:1])=[N:10][CH:9]=[C:8]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=3)=[O:22])[CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 54729996HCID 54729996, compound

Product 1

HCID 54706894HCID 54706894, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

This compound was prepared from ethyl 4-hydroxy-2-oxo-7-(phenylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxylate and cyclopropylamine employing methods similar to those described in Example 5 and using dimethylacetamide as the reaction solvent. The product was obtained as a white solid: 1H NMR (d6-DMSO) δ 11.86 (1H, s), 10.87 (1H, s), 10.14 (1H, s), 8.20 (1H, s), 7.38-7.25 (6H, m), 4.01 (2H, br s), 2.79 (1H, m), 0.70 (2H, m), 0.45 (2H, m); HRMS calcd for C19H17N3O3+H+: 336.1348. Found: 336.1347.

Workup

  1. customThe product was obtained as a white solid

Sources & evidence

ORD record
ord-070b57f0d7394fa28672ab49da1aafe0
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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