N-(3-Aminopropyl)morpholine → HCID 54724626, compound

HRID 2364181Notes

Reaction equation

HRID 2364181 reaction equation
[CH2:1]([C:8]1[CH:17]=[C:16]2[C:11]([C:12]([OH:35])=[C:13]([C:30](OCC)=[O:31])[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.[NH2:36][CH2:37][CH2:38][CH2:39][N:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1>>[CH2:1]([C:8]1[CH:17]=[C:16]2[C:11]([C:12]([OH:35])=[C:13]([C:30]([NH:36][CH2:37][CH2:38][CH2:39][N:40]3[CH2:45][CH2:44][O:43][CH2:42][CH2:41]3)=[O:31])[C:14](=[O:29])[N:15]2[CH2:18][C:19]2[CH:20]=[CH:21][C:22]([S:25]([CH3:28])(=[O:26])=[O:27])=[CH:23][CH:24]=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 61055N-(3-Aminopropyl)morpholineHCID 58882900HCID 58882900, compound

Product 1

HCID 54724626HCID 54724626, 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 N-(3-aminopropyl)morpholine employing methods similar to those described in Example 5 and was obtained as a white solid: 1H NMR (CDCl3) δ 13.29 (1H, br), 10.31 (1H, t, J=6 Hz), 8.62 (1H, d, J=1 Hz), 7.82 (2H, d, J=8.3 Hz), 7.30 (3H, m), 7.18 (2H, d, J=8.3 Hz), 7.07 (1H, s), 7.03 (2H, m), 5.40 (2H, br), 4.32 (2H, m), 4.06 (2H, s), 3.97 (2H, m), 3.60 (2H, m), 3.46 (2H, m), 3.08 (2H, m), 3.02 (3H, s), 2.87 (2H, m), 2.34 (2H, m); HRMS calcd for C31H34N4O6S+H+: 591.2277. Found: 591.2277.

Workup

  1. customwas obtained as a white solid

Sources & evidence

ORD record
ord-44ce9f44fcc040b3b8ec72ad5afd2378
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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