3-Benzyloxy-5-(4-fluoro-benzylcarbamoyl)-4-oxo-1-(2-oxo-ethyl)-1,4-dihydro-pyridine-2-carboxylic acid methyl ester → HCID 54713624, compound
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)CCNC1CCC1.[CH:46]1([N:50]2[CH2:55][CH2:54][C@H:53]([CH3:56])[N:52]3[C:57](=[O:85])[C:58]4[N:59]([CH:61]=[C:62]([C:74]([NH:76][CH2:77][C:78]5[CH:83]=[CH:82][C:81]([F:84])=[CH:80][CH:79]=5)=[O:75])[C:63](=[O:73])[C:64]=4[O:65]CC4C=CC=CC=4)[CH2:60][C@@H:51]23)[CH2:49][CH2:48][CH2:47]1>>[CH:46]1([N:50]2[CH2:55][CH2:54][C@H:53]([CH3:56])[N:52]3[C:57](=[O:85])[C:58]4[N:59]([CH:61]=[C:62]([C:74]([NH:76][CH2:77][C:78]5[CH:83]=[CH:82][C:81]([F:84])=[CH:80][CH:79]=5)=[O:75])[C:63](=[O:73])[C:64]=4[OH:65])[CH2:60][C@@H:51]23)[CH2:47][CH2:48][CH2:49]1Participants
Procedure
In a similar manner to that described in example Z-35a, from 16 (18 mg, 0.39 mmol) and [(3S)-3-Aminobutyl]cyclobutylamine bis hydrochloride (23 mg, 0.107 mmol), (4S,12aS) 1-cyclobutyl-N-[(4-fluorophenyl)methyl]4-methyl-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-37 to give the title compound as a white solid after purification by HPLC (4.5 mg, 25% 2 steps), 1H NMR (CDCl3) δ 12.54 (s, 1H), 10.48 (s, 1H), 8.20 (s, 1H), 7.31 (m, 2H), 6.98 (m, 2H), 5.02 (m, 1H), 4.61-4.57 (m, 2H), 4.26-4.14 (m, 3H), 3.05 (m, 1H), 2.90 (m, 1H), 2.49 (m, 1H), 2.12 (m, 1H), 2.05-1.87 (m, 3H), 1.84-1.61 (m, 3H), 1.46 (m, 1H), 1.32 (m, 3H); ES+ MS: 455 (M+1).
Workup
- customwas prepared as a white solid
Sources & evidence
- ORD record
- ord-225c8014881a4c8c8d6b8539a0d55742
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08778943B2
Reaction notes
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