Ethanolamine → HCID 69482154, compound

HRID 2364539Notes

Reaction equation

HRID 2364539 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:35])=[C:14]([C:30](OCC)=[O:31])[C:15](=[O:29])[N:16]3[CH2:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][C:23]3=[O:28])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[CH2:36]([CH2:38][NH2:39])[OH:37]>>[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:35])=[C:14]([C:30]([NH:39][CH2:38][CH2:36][OH:37])=[O:31])[C:15](=[O:29])[N:16]3[CH2:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][C:23]3=[O:28])=[N:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 700EthanolamineHCID 69480472HCID 69480472, compound

Product 1

HCID 69482154HCID 69482154, compound

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[3-(2-oxo-1-piperidinyl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate and ethanolamine using methods similar to Example 563 to provide an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.64-1.79 (m, 6 H), 2.19 (t, J=6.42 Hz, 2 H), 3.21 (t, J=5.58 Hz, 2 H), 3.33-3.48 (m, 4 H), 3.50-3.61 (m, 2 H), 4.15-4.25 (m, 4 H), 4.93 (t, J=5.05 Hz, 1 H), 7.10-7.18 (m, 2 H), 7.37-7.44 (m, 2 H), 8.00 (d, J=1.26 Hz, 1 H), 8.55 (d, J=1.26 Hz, 1 H), 10.41 (t, J=5.90 Hz, 1 H); ES+ MS: 497 (M+H+).

Workup

  1. customto provide an off-white solid

Sources & evidence

ORD record
ord-795c2df5818e4b508b9c9bcd21864135
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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