1-Propanol, 3-amino-2,2-dimethyl- → 1-[2-(Dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(3-hydroxy-2,2-dimethylpropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364278Notes

Reaction equation

HRID 2364278 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:34]([CH3:38])([CH3:37])[CH2:35][OH:36]>>[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]([OH:23])=[C:7]([C:24]([NH:32][CH2:33][C:34]([CH3:38])([CH3:37])[CH2:35][OH:36])=[O:25])[C:6]1=[O:29]

Participants

3

Reactant 2

HCID 1173261-Propanol, 3-amino-2,2-dimethyl-HCID 58882926HCID 58882926, compound

Product 1

HCID 694811011-[2-(Dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(3-hydroxy-2,2-dimethylpropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

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 3-amino-2,2-dimethyl-1-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 product was obtained as a white solid: 1H NMR (d6-DMSO) δ 10.29 (1H, t, J=6 Hz), 8.51 (1H, s), 7.72 (1H, s), 7.31 (2H, dd, J=9, 5.6 Hz), 7.12 (2H, t, J=9 Hz), 5.13 (2H, s), 4.76 (1H, t, J=5 Hz), 4.11 (2H, s), 3.25 (2H, d, J=6 Hz), 3.17 (2H, d, J=5 Hz), 3.12 (3H, s), 2.82 (3H, s), 0.83 (6H, s); HRMS calcd for C25H29FN4O5+H+: 485.2200. Found: 485.2188.

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-b51b9385d9d6448abade2208684c2fa6
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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