Ethanolamine → HCID 69482022, compound

HRID 2364469Notes

Reaction equation

HRID 2364469 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:34])=[C:14]([C:29](OCC)=[O:30])[C:15](=[O:28])[N:16]3[CH2:19][CH2:20][CH2:21][N:22]3[CH2:26][CH2:25][CH2:24][C:23]3=[O:27])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[CH2:35]([CH2:37][NH2:38])[OH:36]>>[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:34])=[C:14]([C:29]([NH:38][CH2:37][CH2:35][OH:36])=[O:30])[C:15](=[O:28])[N:16]3[CH2:19][CH2:20][CH2:21][N:22]3[CH2:26][CH2:25][CH2:24][C:23]3=[O:27])=[N:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 700EthanolamineHCID 69482189HCID 69482189, compound

Product 1

HCID 69482022HCID 69482022, compound

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[3-(2-oxo-1-pyrrolidinyl)propyl]-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, CDCl3) δ 10.36 (t, J=5.7 Hz, 1 H), 8.53 (s, 1 H), 7.41 (s, 1 H), 7.18 (dd, J=8.3, 5.5 Hz, 2 H), 7.03 (t, J=8.6 Hz, 2 H), 4.16-4.11 (m, 4 H), 3.85 (t, J=5.0 Hz, 2 H), 3.63 (m, 2 H), 3.38-3.33 (m, 4 H), 2.40 (t, J=8.0 Hz, 2 H), 2.03 (m, 2 H), 1.82 (m, 2 H); HRMS C25H27FN4O5 (M+H)+ calcd 483.2044, found 483.2046.

Workup

  1. customwas obtained as a white solid

Sources & evidence

ORD record
ord-6eb15e8ab91f44edbcc90eac8e29c9bd
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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