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
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][CH:41]1[CH2:44][CH2:43][CH2:42]1.O=C1N2CCCNC2CN2C=C(C(N)=O)C(=O)C(OCC3C=CC=CC=3)=C12>>[CH:41]1([N:40]2[CH2:39][CH2:38][C@H:37]([CH3:45])[N:36]3[C:3](=[O:4])[C:5]4[N:6]([CH:7]=[C:8]([C:20]([NH:21][CH2:22][C:23]5[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=5)=[O:30])[C:9](=[O:19])[C:10]=4[OH:11])[CH2:31][C@@H:32]23)[CH2:44][CH2:43][CH2:42]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), 6.08 (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, 8H), 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-975eb63b0625440b9fb5ca3fcaf306ef
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09273065B2
Reaction notes
Loading…