3-Benzyloxy-5-(4-fluoro-benzylcarbamoyl)-4-oxo-1-(2-oxo-ethyl)-1,4-dihydro-pyridine-2-carboxylic acid methyl ester → HCID 54713626, compound

HRID 920702Notes

Reaction equation

COC(C1N(CC=O)C=C(C(=O)NCC2C=CC(F)=CC=2)C(=O)C=1OCC1C=CC=CC=1)=O.Cl.Cl.N[C@@H](C)CCNC.[F:43][C:44]1[CH:49]=[CH:48][C:47]([CH2:50][NH:51][C:52]([C:54]2[C:55](=[O:79])[C:56]([O:71]CC3C=CC=CC=3)=[C:57]3[C:68](=[O:69])[N:61]4[C@@H:62]([CH3:67])[CH2:63][CH2:64][N:65]([CH3:66])[C@@H:60]4[CH2:59][N:58]3[CH:70]=2)=[O:53])=[CH:46][CH:45]=1>>[F:43][C:44]1[CH:49]=[CH:48][C:47]([CH2:50][NH:51][C:52]([C:54]2[C:55](=[O:79])[C:56]([OH:71])=[C:57]3[C:68](=[O:69])[N:61]4[C@@H:62]([CH3:67])[CH2:63][CH2:64][N:65]([CH3:66])[C@@H:60]4[CH2:59][N:58]3[CH:70]=2)=[O:53])=[CH:46][CH:45]=1

Participants

Reactant 3

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

HCID 66594525HCID 66594525, compound

HCID 866372521309562-91-1

Product 1

HCID 54713626HCID 54713626, compoundYield 44%

Procedure

In a similar manner to that described in example Z-35, from 16 (18 mg, 0.0398 mmol) and [(3S)-3-aminobutyl]methylamine bis-hydrochloride (10 mg, 0.109 mmol, (4S,12aS)-N-[(4-fluorophenyl)methyl]-1,4-dimethyl-6,8-dioxo-7-[(phenylmethyl)oxy]-1,2,3,4,6,8,12,12a-octahydropyrido[1′,2′:4,5]pyrazino[1,2-a]pyrimidine-9-carboxamide was prepared as a white solid. This material was deprotected in a second step similar to that described in example Z-87 to give the title compound as a tan solid (7 mg, 44% 2 steps). 1H NMR (CDCl3) δ 12.53 (s, 1H), 10.47 (s, 1H), 8.29 (s, 1H), 7.32 (m, 2H), 6.99 (m, 2H), 5.04 (1H), 4.60 (m, 2H), 4.28 (s, 3H), 2.88-2.80 (m, 2H), 2.32 (s, 3H), 2.18 (m, 1H), 1.48 (m, 1H), 1.34 (m, 3H); ES+MS: 415 (M+1).

Workup

customwas prepared as a white solid

Sources & evidence

ORD record: ord-d2291ff20d474cacb9ed435d6ed393fc
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273065B2

Reaction notes

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