Triethylamine → HCID 69482760, compound

HRID 2364328Notes

Reaction equation

HRID 2364328 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.Cl.[NH2:28][CH2:29][C:30]1([OH:36])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.C(N(CC)CC)C>>[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:28][CH2:29][C:30]4([OH:36])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]4)=[O:22])[C:15](=[O:20])[N:16]3[CH3:19])=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 3084332Cyclohexanol, 1-(aminomethyl)-, hydrochloride (1:1)HCID 54730000Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 69482760HCID 69482760, compoundYield 18.2%

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, 1-(aminomethyl)cyclohexanol hydrochloride (110 mg, 0.66 mmol) and triethylamine (0.28 mL, 1.98 mmol), was prepared 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[(1-hydroxycyclohexyl)methyl]-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (4 mg, 18% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.46 (br s, 1 H), 8.55 (s, 1 H), 7.38 (s, 1 H), 7.17-7.13 (m, 2 H), 7.04-6.94 (m, 2 H), 4.12 (s, 2 H), 3.58 (s, 3 H), 3.48 (d, J=5.6 Hz, 2 H), 1.62-1.49 (m, 1 H); MS m/z 440 (M+1).

Sources & evidence

ORD record
ord-05615b668dc34325b940731f5dcaa13f
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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