1-Aminocyclopentanemethanol → HCID 69480289, compound

HRID 2364329Notes

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:26])=[C:14]([C:21](OCC)=[O:22])[C:15](=[O:20])[N:16]3[CH3:19])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[NH2:27][C:28]1([CH2:33][OH:34])[CH2:32][CH2:31][CH2:30][CH2:29]1>>[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:26])=[C:14]([C:21]([NH:27][C:28]4([CH2:33][OH:34])[CH2:32][CH2:31][CH2:30][CH2:29]4)=[O:22])[C:15](=[O:20])[N:16]3[CH3:19])=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 663071-Aminocyclopentanemethanol

HCID 54730000Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 69480289HCID 69480289, compoundYield 48%

Procedure

In a similar manner to that described in example 196, from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (18 mg, 0.050 mmol) described in example 92 and (1-aminocyclopentyl)methanol (76 mg, 0.66 mmol) was prepared 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[1-(hydroxymethyl)cyclopentyl]-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide(10 mg, 48% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.56 (br s, 1H), 8.55 (s, 1 H), 7.37 (s, 1 H), 7.17-7.14 (m, 2 H), 7.04-6.99 (m, 2 H), 4.12 (s, 2 H), 3.78 (s, 2 H), 3.56 (s, 3 H), 1.98-1.68 (m, 8 H); MS m/z 424 (M−1).

Sources & evidence

ORD record: ord-f5197b0c0fc84c3a981c31833c93ef05
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691991B2

Reaction notes

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