Ethanolamine → HCID 69480293, compound

HRID 2364310Notes

Reaction equation

HRID 2364310 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:32])=[C:14]([C:27](OCC)=[O:28])[C:15](=[O:26])[N:16]3[CH2:19][CH2:20][NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[CH2:33]([CH2:35][NH2:36])[OH:34]>>[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:32])=[C:14]([C:27]([NH:36][CH2:35][CH2:33][OH:34])=[O:28])[C:15](=[O:26])[N:16]3[CH2:19][CH2:20][NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 700EthanolamineHCID 69482669HCID 69482669, compound

Product 1

HCID 69480293HCID 69480293, compound

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-{2-[(methylsulfonyl)amino]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and ethanolamine employing methods similar to those described in Example 202 and was obtained as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 10.38 (t, J=5.2 Hz, 1 H), 8.55 (s, 1 H), 8.10 (s, 1 H), 7.40 (dd, J=8.2, 5.7 Hz, 2 H), 7.27 (t, J=6.1 Hz, 1 H), 7.13 (t, J=8.8 Hz, 2 H), 4.95 (t, J=5.0 Hz, 1 H), 4.34 (t, J=6.3 Hz, 2 H), 4.14 (s, 2 H), 3.57 (m, 2 H), 3.45 (m, 2 H), 3.24 (m, 2 H), 2.89 (s, 3 H); HRMS C21H23FN4O6S (M+H)+ calcd 479.1322, found 479.1400.

Workup

  1. customwas obtained as a white solid

Sources & evidence

ORD record
ord-aa69419d409849cbb07167c12c799bf4
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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