Cyclobutylamine → HCID 54676800, compound

HRID 2364179Notes

Reaction equation

HRID 2364179 reaction equation
[CH2:1]([C:8]1[CH:17]=[C:16]2[C:11]([C:12]([OH:28])=[C:13]([C:23](OCC)=[O:24])[C:14](=[O:22])[N:15]2[CH2:18][CH:19]2[CH2:21][CH2:20]2)=[N:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:29]1([NH2:33])[CH2:32][CH2:31][CH2:30]1>>[CH2:1]([C:8]1[CH:17]=[C:16]2[C:11]([C:12]([OH:28])=[C:13]([C:23]([NH:33][CH:29]3[CH2:32][CH2:31][CH2:30]3)=[O:24])[C:14](=[O:22])[N:15]2[CH2:18][CH:19]2[CH2:21][CH2:20]2)=[N:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 75645CyclobutylamineHCID 58882910HCID 58882910, compound

Product 1

HCID 54676800HCID 54676800, compound

Procedure

This compound was prepared from ethyl 7-benzyl-1-(cyclopropylmethyl)-4-hydroxy-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 10.34 (1H, br d, J=7 Hz), 8.59 (1H, s), 7.46 (1H, s), 7.35 (2H, t, J=7 Hz), 7.28 (1H, t, J=7 Hz), 7.21 (2H, d, J=7 Hz), 4.53 (1H, m), 4.17 (2H, s), 4.08 (2H, d, J=7 Hz), 2.42 (2H, m), 2.09 (2H, m), 1.80 (2H, m), 1.01 (1H, m), 0.50 (2H, m), 0.40 (2H, m); HRMS calcd for C24H25N3O3+H+: 404.1974. Found: 404.1971.

Workup

  1. customwas obtained as an off-white solid

Sources & evidence

ORD record
ord-eb2c516550254f218fb30eaa16813d28
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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