Cyclobutylamine → HCID 54716982, compound

HRID 2364190Notes

Reaction equation

HRID 2364190 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)[N:5]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)[C:4](=[O:29])[C:3]=1[C:30]([O:32]CC)=O.[CH:35]1([NH2:39])[CH2:38][CH2:37][CH2:36]1>>[CH:35]1([NH:39][C:30]([C:3]2[C:4](=[O:29])[N:5]([CH2:19][C:20]3[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=3)[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:32])[CH2:38][CH2:37][CH2:36]1

Participants

3

Reactant 2

HCID 75645CyclobutylamineHCID 58882992HCID 58882992, compound

Product 1

HCID 54716982HCID 54716982, compound

Procedure

This compound was prepared from ethyl 4-hydroxy-1-[(4-nitrophenyl)methyl]-2-oxo-7-(phenylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxylate and cyclobutylamine employing methods similar to those described in Example 2 and was obtained as a white solid: 1H NMR (d6-DMSO) δ 10.91 (1H, d, J=7.6 Hz), 8.21 (1H, s), 8.10 (2H, d, J=8.6 Hz), 7.35 (2H, d, J=8.6 Hz), 7.29 (1H, s), 7.14 (3H, m), 7.08 (2H, m), 5.47 (2H, br s), 4.40 (1H, m), 3.91 (2H, s), 2.24 (2H, m), 1.86 (2H, m), 1.67 (2H, m); HRMS calcd for C27H24N4O5+H+: 485.1825. Found: 485.1815.

Workup

  1. customwas obtained as a white solid

Sources & evidence

ORD record
ord-539b1afcbc0d4f88882e427a66140342
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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