Methylamine → HCID 69482441, compound

HRID 2364250Notes

Reaction equation

HRID 2364250 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]([O:30]CC)=O)[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.[CH3:34][NH2:35]>>[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:35][CH3:34])=[O:30])[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 6329MethylamineHCID 58882934HCID 58882934, compound

Product 1

HCID 69482441HCID 69482441, 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 methylamine 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 14.3 (1H, br), 9.94 (1H, m), 8.54 (1H, s), 7.14 (3H, m), 7.02 (2H, t, J=8.6 Hz), 4.86 (2H, s), 4.11 (2H, s), 3.51 (2H, t, J=7 Hz), 3.46 (2H, t, J=7 Hz), 2.99 (3H, d, J=5 Hz), 2.05 (2H, m, J=7 Hz), 1.89 (2H, m, J=7 Hz); HRMS calcd for C23H23FN4O4+H+: 439.1782. Found: 439.1794.

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-7ad1ada2f5a04f0485b5d144883eb903
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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