Cyclobutylamine → HCID 54713582, compound

HRID 2364171Notes

Reaction equation

HRID 2364171 reaction equation
[CH2:1]([C:8]1[CH:17]=[C:16]2[C:11]([C:12]([OH:35])=[C:13]([C:30]([O:32]CC)=O)[C:14](=[O:29])[N:15]2[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)=[N:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:36]1([NH2:40])[CH2:39][CH2:38][CH2:37]1>>[CH2:1]([C:8]1[CH:17]=[C:16]2[C:11]([C:12]([OH:35])=[C:13]([C:30]([NH:40][CH:36]3[CH2:39][CH2:38][CH2:37]3)=[O:32])[C:14](=[O:29])[N:15]2[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:26])=[O:27])=[CH:21][CH:20]=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 58882900HCID 58882900, compound

Product 1

HCID 54713582HCID 54713582, compound

Procedure

This compound was prepared from ethyl 7-benzyl-4-hydroxy-1-[4-(methylsulfonyl)benzyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and cyclobutylamine employing methods similar to those described in Example 2. The product was obtained as a white solid: 1H NMR (CDCl3) δ 10.19 (1H, br d, J=7.4 Hz), 8.61 (1H, d, J=1.1 Hz), 7.82 (2H, d, J=8.4 Hz), 7.30 (3H, m), 7.18 (2H, d, J=8.4 Hz),7.06 (1H, s), 7.03 (2H, m), 5.41 (2H, br), 4.54 (1H, m), 4.05 (2H, s), 3.02 (3H, s), 2.44 (2H, m), 2.08 (2H, m), 1.83 (2H, m); HRMS calcd for C28H27N3O5S+H+: 518.1740. Found: 518.1741.

Workup

  1. customThe product was obtained as a white solid

Sources & evidence

ORD record
ord-4be9d5c62f4840c584e0727a45a3ed67
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

Loading…