3-Benzyloxy-5-(4-fluoro-benzylcarbamoyl)-4-oxo-1-(2-oxo-ethyl)-1,4-dihydro-pyridine-2-carboxylic acid methyl ester → HCID 54713623, compound

HRID 920699Notes

Reaction equation

HRID 920699 reaction equation
CO[C:3]([C:5]1[N:6]([CH2:31][CH:32]=O)[CH:7]=[C:8]([C:20](=[O:30])[NH:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[C:9](=[O:19])[C:10]=1[O:11]CC1C=CC=CC=1)=[O:4].Cl.Cl.[NH2:36][C@@H:37]([CH3:45])[CH2:38][CH2:39][NH:40][CH2:41][CH2:42][O:43][CH3:44]>CO.ClCCl>[F:29][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][NH:21][C:20]([C:8]2[C:9](=[O:19])[C:10]([OH:11])=[C:5]3[C:3](=[O:4])[N:36]4[C@@H:37]([CH3:45])[CH2:38][CH2:39][N:40]([CH2:41][CH2:42][O:43][CH3:44])[C@@H:32]4[CH2:31][N:6]3[CH:7]=2)=[O:30])=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 596005723-Benzyloxy-5-(4-fluoro-benzylcarbamoyl)-4-oxo-1-(2-oxo-ethyl)-1,4-dihydro-pyridine-2-carboxylic acid methyl esterHCID 86637250HCID 86637250, compound

Product 1

HCID 54713623HCID 54713623, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

In a manner similar to that described in example Z-36, from 16 (15 mg, 0.034 mmol) and [(3S)-3-Aminobutyl][2(methyloxy)ethyl]amine bis hydrochloride (19 mg, 0.087 mmol), (4S,12aS)-N-[(4-fluorophenyl)methyl]-4-methyl-1-[2-(methyloxy)ethyl]-6,8-dioxo-7-[(phenylmethyl)oxy]-1,2,8,4,6,8,12,12a-octahydropyrido[1′,2′:4,5]pyrazino[1,2-a]pyrimidine-9-carboxamide was prepared as a white solid after silica gel chromatography (1-12% methanol/dichloromethane). This material was deprotected in a second step similar to that described in example Z-37 to give the title compound as a yellow solid (9 mg, 60%, 2 steps). 1H NMR (CDCl3) δ 12.56 (s, 1H), 10.51 (m, 1H), 8.29 (s, 1H), 7.32 (m, 2H), 6.98 (m, 2H), 5.08 (m, 1H), 4.65-4.59 (m, 2H), 4.53 (m, 1H), 4.21 (m, 1H), 3.61-3.40 (m, 2H), 3.34-3.13 (m, 8H), 3.08 (m, 1H), 2.04-2.84 (m, 2H), 2.68 (m, 1H), 2.07 (m, 1H), 1.50 (m, 1H), 1.35 (d, J=7.2 Hz, 3H), 1.14 (m, 1H); ES+MS: 459 (M+1).

Sources & evidence

ORD record
ord-fd8ff7bc6f234c97843b9ccde909e3a3
Source dataset
uspto-grants-2016_03
Patent number
US09273065B2

Reaction notes

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