Triethylamine → HCID 69482613, compound

HRID 2364330Notes

Reaction equation

HRID 2364330 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.C(N(CC)CC)C.Cl.[NH2:35][CH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH:37]1[OH:42]>>[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:26])=[C:14]([C:21]([NH:35][CH:36]4[CH2:41][CH2:40][CH2:39][CH2:38][CH:37]4[OH:42])=[O:22])[C:15](=[O:20])[N:16]3[CH3:19])=[N:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 218772022-Aminocyclohexanol hydrochlorideHCID 54730000Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 69482613HCID 69482613, compoundYield 38%

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, triethylamine (0.3 mL, 1.95 mmol), and 2-aminocyclohexanol hydrochloride (100 mg, 0.66 mmol), was prepared 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxycyclohexyl)-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (8 mg, 38% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.29 (d, J=7.6 Hz, 1 H), 8.54 (s, 1 H), 7.37 (s, 1 H), 7.17-7.13 (m, 2 H), 7.04-6.99 (m, 2 H), 4.12 (s, 2 H), 3.86 (m, 1 H), 3.56-3.47 (m, 4 H), 2.07 (m, 2 H), 1.75 (m, 2 H), 1.42-1.23 (m, 4 H); HRMS m/z calcd for C23H25N3O4F: 426.1829 Found: 426.1834.

Sources & evidence

ORD record
ord-bf2a79624d954001ba6d712847e501fe
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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