Cyclobutylamine → HCID 54723970, compound

HRID 2364183Notes

Reaction equation

HRID 2364183 reaction equation
[CH2:1]([C:8]1[CH:17]=[C:16]2[C:11]([C:12]([OH:30])=[C:13]([C:25]([O:27]CC)=O)[C:14](=[O:24])[N:15]2[CH2:18][C:19]2[S:20][CH:21]=[CH:22][N:23]=2)=[N:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:31]1([NH2:35])[CH2:34][CH2:33][CH2:32]1>>[CH2:1]([C:8]1[CH:17]=[C:16]2[C:11]([C:12]([OH:30])=[C:13]([C:25]([NH:35][CH:31]3[CH2:34][CH2:33][CH2:32]3)=[O:27])[C:14](=[O:24])[N:15]2[CH2:18][C:19]2[S:20][CH:21]=[CH:22][N:23]=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 58882970HCID 58882970, compound

Product 1

HCID 54723970HCID 54723970, compound

Procedure

This compound was prepared from ethyl 7-benzyl-4-hydroxy-2-oxo-1-(1,3-thiazol-2-ylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxylate and cyclobutylamine employing methods similar to those described in Example 5 and was obtained as a white solid: 1H NMR (d6-DMSO) δ 10.27 (1H, d, J=7), 8.56 (1H, s), 8.13 (1H, s), 7.70 (1H, d, J=3.2 Hz), 7.67 (1H, d, J=3.2 Hz), 7.28-7.16 (5H, m), 5.78 (2H, s), 4.41 (1H, m), 4.09 (2H, s), 2.29 (2H, m), 2.05 (2H, m), 1.71 (2H, m); HRMS calcd for C24H22N4O3S+H+: 447.1491. Found: 447.1487.

Workup

  1. customwas obtained as a white solid

Sources & evidence

ORD record
ord-5f6960f4432042f987d99948b379e57d
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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