Ethanolamine → HCID 58882918, compound

HRID 2364207Notes

Reaction equation

HRID 2364207 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](OCC)=[O:29])[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.[CH2:34]([CH2:36][NH2:37])[OH: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:37][CH2:36][CH2:34][OH:35])=[O:29])[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:6][CH:7]=1

Participants

3

Reactant 2

HCID 700EthanolamineHCID 58882934HCID 58882934, compound

Product 1

HCID 58882918HCID 58882918, 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 ethanolamine 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 (d6-DMSO) δ 10.27 (1H, t, J=5 Hz), 8.51 (1H, s), 7.75 (1H, s), 7.31 (2H, dd, J=9, 6 Hz), 7.12 (2H, t, J=9 Hz), 5.03 (2H, s), 4.90 (1H, br), 4.12 (2H, s), 3.58 (2H, t, J=6 Hz), 3.54 (2H, m), 3.42 (2H, t, J=7 Hz), 3.40 (2H, t, J=7 Hz), 1.96 (2H, m, J=7 Hz), 1.80 (2H, m, J=7 Hz); HRMS calcd for C24H25FN4O5+H+: 469.1887. Found: 469.1896.

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-eaf4c8dcf9a947bd8bd56204d89d63ab
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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