Ethanolamine → HCID 69480867, compound

HRID 2364552Notes

Reaction equation

HRID 2364552 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:28](OC)=[O:29])[C:15](=[O:27])[N:16]3[C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[NH2:33][CH2:34][CH2:35][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:32])=[C:14]([C:28]([NH:33][CH2:34][CH2:35][OH:36])=[O:29])[C:15](=[O:27])[N:16]3[C:19]3[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=3)=[N:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 700EthanolamineHCID 69480433HCID 69480433, compound

Product 1

HCID 69480867HCID 69480867, compoundYield 89%

Procedure

In a similar manner to that described in example 196, from methyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-[4-(methyloxy)phenyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (50 mg, 0.115 mmol) and 2-aminoethanol (0.03 mL) was prepared 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-1-[4-(methyloxy)phenyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (47 mg, 89% yield) as a white solid. 1H NMR (CDCl3) δ 10.18 (s, 1 H), 8.44 (s, 1 H), 7.08-7.02 (m, 4 H), 6.98-6.94 (m, 2 H), 6.91-6.87 (m, 2 H), 6.74 (s, 1 H), 3.90 (s, 2 H), 3.85 (s, 3 H), 3.71 (m, 2 H), 3.53 (m, 2 H); HRMS m/z calcd for C25H23FN3O5: 464.1616 Found: 464.1617.

Sources & evidence

ORD record
ord-791e7b1f0bdd4c28a590f24ba901d59e
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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