1-Aminocyclopentanemethanol → HCID 69482705, compound

HRID 2364376Notes

Reaction equation

HRID 2364376 reaction equation
[CH3:1][N:2]([CH3:31])[C:3](=[O:30])[CH2:4][N:5]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:13]=2)[C:8]([OH:23])=[C:7]([C:24](OCC)=[O:25])[C:6]1=[O:29].[NH2:32][C:33]1([CH2:38][OH:39])[CH2:37][CH2:36][CH2:35][CH2:34]1>>[CH3:1][N:2]([CH3:31])[C:3](=[O:30])[CH2:4][N:5]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:13]=2)[C:8]([OH:23])=[C:7]([C:24]([NH:32][C:33]2([CH2:38][OH:39])[CH2:37][CH2:36][CH2:35][CH2:34]2)=[O:25])[C:6]1=[O:29]

Participants

3

Reactant 2

HCID 663071-AminocyclopentanemethanolHCID 58882926HCID 58882926, compound

Product 1

HCID 69482705HCID 69482705, compound

Procedure

This compound was prepared from ethyl 1-[2-(dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and (1-aminocyclopentyl)methanol employing methods similar to those described in Example 245 and was purified by reverse phase preparative HPLC (C-18 stationary phase; 10-100% CH3CN/water/0.1% formic acid mobile phase). The product was obtained as a cream-colored solid: 1H NMR (d6-DMSO) δ 10.32 (1H, s), 8.50 (1H, s), 7.74 (1H, s), 7.32 (2H, dd, J=8.5, 6 Hz), 7.12 (2H, t, J˜9 Hz), 5.12 (2H, s), 5.04 (1H, br), 4.11 (2H, s), 3.51 (2H, s), 3.12 (3H, s), 2.82 (3H, s), 1.91 (2H, m), 1.74 (4H, m), 1.56 (2H, m); HRMS calcd for C26H29FN4O5+H+: 497.2200. Found: 497.2200.

Workup

  1. customwas purified by reverse phase preparative HPLC (C-18 stationary phase; 10-100% CH3CN/water/0.1% formic acid mobile phase)
  2. customThe product was obtained as a cream-colored solid

Sources & evidence

ORD record
ord-144387f5fbb2462f9fdfbdba47512851
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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