Cyclobutylamine → HCID 54713574, compound

HRID 2364180Notes

Reaction equation

HRID 2364180 reaction equation
[CH2:1]([C:8]1[CH:17]=[C:16]2[C:11]([C:12]([OH:32])=[C:13]([C:27](OCC)=[O:28])[C:14](=[O:26])[N:15]2[CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[N:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:33]1([NH2:37])[CH2:36][CH2:35][CH2:34]1>>[CH2:1]([C:8]1[CH:17]=[C:16]2[C:11]([C:12]([OH:32])=[C:13]([C:27]([NH:37][CH:33]3[CH2:36][CH2:35][CH2:34]3)=[O:28])[C:14](=[O:26])[N:15]2[CH2:18][CH2:19][N:20]2[CH2:21][CH2:22][O:23][CH2:24][CH2:25]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 75645CyclobutylamineHCID 58882987HCID 58882987, compound

Product 1

HCID 54713574HCID 54713574, compound

Procedure

This compound was prepared from ethyl 7-benzyl-4-hydroxy-1-(2-morpholin-4-ylethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and cyclobutylamine employing methods similar to those described in Example 5 and was obtained as an off-white solid: 1H NMR (CDCl3) δ 10.01 (1H, br d, J=5 Hz), 8.70 (1H, s), 8.61 (1H, s), 7.39 (2H, d, J=7.7 Hz), 7.30 (2H, t, J=7.7 Hz), 7.21 (1H, m), 4.89 (2H, m), 4.52 (1H, m), 4.26 (4H, m), 4.07 (2H, m), 3.50 (2H, m), 3.18 (2H, m), 3.09 (2H, m), 2.43 (2H, m), 2.06 (2H, m), 1.81 (2H, m); HRMS calcd for C26H30N4O4+H+: 463.2345. Found: 463.2343.

Workup

  1. customwas obtained as an off-white solid

Sources & evidence

ORD record
ord-8527d277cb97431c8e64d5753b237e81
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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