Cyclobutylamine → HCID 69482808, compound

HRID 2364433Notes

Reaction equation

HRID 2364433 reaction equation
[CH:1]1([NH:4][C:5](=[O:32])[CH2:6][N:7]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([CH2:17][C:18]4[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=4)[CH:15]=3)[C:10]([OH:25])=[C:9]([C:26]([O:28]CC)=O)[C:8]2=[O:31])[CH2:3][CH2:2]1.[CH:33]1([NH2:37])[CH2:36][CH2:35][CH2:34]1>>[CH:33]1([NH:37][C:26]([C:9]2[C:8](=[O:31])[N:7]([CH2:6][C:5]([NH:4][CH:1]3[CH2:2][CH2:3]3)=[O:32])[C:16]3[C:11]([C:10]=2[OH:25])=[N:12][CH:13]=[C:14]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH:15]=3)=[O:28])[CH2:36][CH2:35][CH2:34]1

Participants

3

Reactant 2

HCID 75645CyclobutylamineHCID 69482711HCID 69482711, compound

Product 1

HCID 69482808HCID 69482808, compound

Procedure

This compound was prepared from ethyl 1-[2-(cyclopropylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and cyclobutylamine by methods similar to those described in Example 245. The crude material was triturated with a mixture of MeOH and 1N HCl to afford the product as a white solid: 1H NMR (d6-DMSO) δ 10.30 (1H, d, J=7 Hz), 8.54 (1H, s), 8.24 (1H, d, J=4 Hz), 7.74 (1H, s), 7.32 (2H, dd, J=8.4, 5.7 Hz), 7.11 (2H, t, J˜9 Hz), 4.80 (2H, s), 4.40 (1H, m, J=8 Hz), 4.11 (2H, s), 2.56 (1H, m), 2.29 (2H, m), 2.03 (2H, m), 1.71 (2H, m), 0.59 (2H, m), 0.36 (2H, m); HRMS calcd for C25H25FN4O4+H+: 465.1938. Found: 465.1934.

Workup

  1. customThe crude material was triturated with a mixture of MeOH and 1N HCl

Sources & evidence

ORD record
ord-c0c30337708f499da075360e521d3573
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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