2-Aminopropanol → HCID 69480176, compound

HRID 2364268Notes

Reaction equation

HRID 2364268 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:33])=[C:14]([C:28](OCC)=[O:29])[C:15](=[O:27])[N:16]3[CH2:19][C:20](=[O:26])[N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[NH2:34][CH:35]([CH3:38])[CH2:36][OH:37]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:33])=[C:14]([C:28]([NH:34][CH:35]([CH3:38])[CH2:36][OH:37])=[O:29])[C:15](=[O:27])[N:16]3[CH2:19][C:20](=[O:26])[N:21]3[CH2:22][CH2:23][CH2:24][CH2:25]3)=[N:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 51262-AminopropanolHCID 58882934HCID 58882934, compound

Product 1

HCID 69480176HCID 69480176, compound

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[2-oxo-2-(1-pyrrolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate and (±)-2-amino-1-propanol employing methods similar to those those described in Example 9 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 white solid: 1H NMR (CDCl3) δ 10.16 (1H, d, J=8 Hz), 8.54 (1H, s), 7.15 (2H, dd, J=8.5, 5.3 Hz), 7.04 (1H, s), 7.02 (2H, t, J=8.5 Hz), 4.90 (1H, d, J=17 Hz), 4.83 (1H, d, J=17 Hz), 4.27 (1H, m), 4.11 (2H, s), 3.76 (1H, m), 3.66 (1H, m), 3.50-3.44 (4H, m), 2.24 (1H, br), 2.05 (2H, m, J=7 Hz), 1.89 (2H, m, J=7 Hz), 1.29 (3H, d, J=7 Hz); HRMS calcd for C25H27FN4O5+H+: 483.2044. Found: 483.2047.

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 white solid

Sources & evidence

ORD record
ord-7335bb4539e142139553f8f606b77021
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

Loading…