2-(Propan-2-yloxy)ethan-1-amine → HCID 69482564, compound

HRID 2364316Notes

Reaction equation

HRID 2364316 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].[CH3:32][CH:33]([O:35][CH2:36][CH2:37][NH2:38])[CH3:34]>>[CH3:31][N:2]([CH3:1])[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:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[CH:13]=2)[C:8]([OH:23])=[C:7]([C:24]([NH:38][CH2:37][CH2:36][O:35][CH:33]([CH3:34])[CH3:32])=[O:25])[C:6]1=[O:29]

Participants

3

Reactant 2

HCID 5338662-(Propan-2-yloxy)ethan-1-amineHCID 58882926HCID 58882926, compound

Product 1

HCID 69482564HCID 69482564, 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 2-[(1-methylethyl)oxy]ethanamine 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 white solid: 1H NMR (d6-DMSO) δ 10.67 (1H, br), 8.16 (1H, br s), 7.27 (3H, m), 7.10 (2H, t, J=9 Hz), 4.93 (2H, s), 4.00 (2H, s), 3.54 (1H, m, J=6 Hz), 3.40 (2H, m), 3.31 (2H, m), 3.08 (3H, s), 2.78 (3H, s), 1.08 (6H, d, J=6 Hz); HRMS calcd for C25H29FN4O5+H+: 485.2200. Found: 485.2205.

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-3e5864d04daf466fbb945e03669b135a
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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