Tetrahydrofurfurylamine → HCID 69482783, compound

HRID 2364474Notes

Reaction equation

[F:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][C:7]2[CH:16]=[C:15]3[C:10]([C:11]([OH:31])=[C:12]([C:26](OCC)=[O:27])[C:13](=[O:25])[N:14]3[CH2:17][CH2:18][N:19]3[CH2:23][CH2:22][CH2:21][C:20]3=[O:24])=[N:9][CH:8]=2)=[CH:4][CH:3]=1.[O:34]1[CH2:38][CH2:37][CH2:36][CH:35]1[CH2:39][NH2:40]>>[F:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][C:7]2[CH:16]=[C:15]3[C:10]([C:11]([OH:31])=[C:12]([C:26]([NH:40][CH2:39][CH:35]4[CH2:36][CH2:37][CH2:38][O:34]4)=[O:27])[C:13](=[O:25])[N:14]3[CH2:17][CH2:18][N:19]3[CH2:23][CH2:22][CH2:21][C:20]3=[O:24])=[N:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 253298Tetrahydrofurfurylamine

HCID 58882907Ethyl 7-(4-fluorobenzyl)-4-hydroxy-2-oxo-1-[2-oxopyrrolidin-1-yl ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 69482783HCID 69482783, compound

Procedure

This compound was prepared from ethyl 7-(4-fluorobenzyl)-4-hydroxy-2-oxo-1-[2-(2-oxopyrrolidin-1-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate and (tetrahydro-2-furanylmethyl)amine using conditions similar to those employed in Example 563 to provide a white solid: 1H NMR (d6-DMSO) δ 10.39 (1H, t, J=6 Hz), 8.55 (1H, s), 8.12 (1H, s), 7.40 (2H, dd, J=6, 9 Hz), 7.13 (2H, t, J=9 Hz), 4.38 (2H, b), 4.15 (2H, s), 3.95-4.02 (1H, m), 3.80 (1H, q, J=8 Hz), 3.66 (1H, q, J=8 Hz), 3.50-3.57 (1H, m), 3.32-3.46 (5H, m), 1.89-1.99 (3H, m), 1.78-1.87 (2H, m), 1.70-1.78 (2H, m), 1.49-1.58 (1H, m); ES+ MS: 509 (+H+).

Workup

customto provide a white solid

Sources & evidence

ORD record: ord-96b585b96bab44179da6dca2e74af652
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691991B2

Reaction notes

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