Sodium Hydroxide → HCID 69482698, compound

HRID 2364381Notes

Reaction equation

HRID 2364381 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][CH2:33][C@H:34]([OH:36])[CH3:35].[OH-].[Na+:38]>>[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:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[CH:13]=2)[C:8]([O-:23])=[C:7]([C:24]([NH:32][CH2:33][C@H:34]([OH:36])[CH3:35])=[O:25])[C:6]1=[O:29].[Na+:38]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 439938(2R)-1-aminopropan-2-olHCID 58882926HCID 58882926, compound

Product 1

HCID 69482698HCID 69482698, 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 (2R)-1-amino-2-propanol 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 resulting material was treated with 1.3 equivalents of 1N NaOH solution and triturated with CH3CN to afford the product as a white solid: 1H NMR (d6-DMSO) δ 10.59 (1H, br), 8.14 (1H, s), 7.26 (3H, m), 7.10 (2H, m), 4.92 (2H, s), 4.80 (1H, br), 3.99 (2H, s), 3.67 (1H, br), 3.15 (2H, m), 3.08 (3H, s), 2.78 (3H, s), 1.04 (3H, br d, J˜5 Hz); HRMS calcd for C23H25FN4O5+H+: 457.1887. Found: 457.1882.

Workup

  1. customwas purified by reverse phase preparative HPLC (C-18 stationary phase; 10-100% CH3CN/water/0.1% formic acid mobile phase)
  2. customtriturated with CH3CN

Sources & evidence

ORD record
ord-1b80313829cf48468351fed895056593
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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