1-Amino-2-propanol → HCID 69482802, compound

HRID 2364235Notes

Reaction equation

HRID 2364235 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:34])=[C:14]([C:29](OCC)=[O:30])[C:15](=[O:28])[N:16]3[CH2:19][C:20](=[O:27])[N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[NH2:35][CH2:36][CH:37]([OH:39])[CH3:38]>>[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:34])=[C:14]([C:29]([NH:35][CH2:36][CH:37]([OH:39])[CH3:38])=[O:30])[C:15](=[O:28])[N:16]3[CH2:19][C:20](=[O:27])[N:21]3[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 41-Amino-2-propanolHCID 69480365HCID 69480365, compound

Product 1

HCID 69482802HCID 69482802, compound

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[2-oxo-2-(1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate and (±)-1-amino-2-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 10.32 (1H, m), 8.55 (1H, s), 7.16 (2H, dd, J=8.5, 5.5 Hz), 7.03 (2H, t, J=8.5 Hz), 6.97 (1H, s), 4.94 (2H, m), 4.11 (2H, s), 4.04 (1H, m), 3.62 (1H, m), 3.50 (2H, t, J=5.5 Hz), 3.44 (2H, t, J=5.5 Hz), 3.35 (1H, m), 2.21 (1H, d, J=4 Hz), 1.69 (2H, m), 1.54 (4H, m), 1.26 (3H, d, J=6 Hz); HRMS calcd for C26H29FN4O5+H+: 497.2200. Found: 497.2189.

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-f1b59c10249b459fba8591f1889efebe
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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