(S)-2-(Piperidin-2-yl)ethanamine → HCID 54713622, compound
Reaction equation
C1N2C3N(C=C4C=CC(C(N)=O)=CN4C=3)C=CC2=CC=C1.N1CCCC[C@H]1CCN.[F:31][C:32]1[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=1[CH2:39][NH:40][C:41]([C:43]1[C:44](=[O:70])[C:45]([O:62]CC2C=CC=CC=2)=[C:46]2[C:59](=[O:60])[N:50]3[CH2:51][CH2:52][C@@H:53]4[CH2:58][CH2:57][CH2:56][CH2:55][N:54]4[C@@H:49]3[CH2:48][N:47]2[CH:61]=1)=[O:42]>>[F:31][C:32]1[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=1[CH2:39][NH:40][C:41]([C:43]1[C:44](=[O:70])[C:45]([OH:62])=[C:46]2[C:59](=[O:60])[N:50]3[CH2:51][CH2:52][C@@H:53]4[CH2:58][CH2:57][CH2:56][CH2:55][N:54]4[C@@H:49]3[CH2:48][N:47]2[CH:61]=1)=[O:42]Participants
Procedure
(4S,12aS)—N-[(2,4-Difluorophenyl)methyl]-9-hydroxy-8,10-dioxo-2,3,4,4a,5,6,8,10,14,14a-decahydro, 1H-pyrido[1,2-c]pyrido[1′,2′:4,5]pyrazino[1,2-a]pyrimidine-11-carboxamide. In a manner similar to that described in example Z-35, from {2-[(2S)-2-piperidinyl]ethyl}amine (28 mg, 0.218 mmol) and 16a (30 mg, 0.0638 mmol) was prepared (4aS,14aS)—N-[(2,4-difluorophenyl)methyl]-8,10-dioxo-9-[(phenylmethyl)oxy]-2,3,4,4a,5,6,8,10,14,14a-decahydro-1H-pyrido[1,2-c]pyrido[1′,2′:4,5]pyrazino[1,2-a]pyrimidine-11-carboxamide (29 mg, 82%). 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 (26 mg, quantitative). 1H NMR (CDCl3) δ 12.44 (br s, 1H), 10.48 (s, 1H), 8.26 (s, 1H), 7.35 (m, 1H), 6.80 (m, 2H), 4.68-4.57 (m, 2H), 4.38 (m, 1H), 4.20 (m, 1H), 3.93 (s, 1H), 3.63-3.39 (m, 2H), 2.91 (m, 2H), 2.29 (br s, 1H), 2.02 (m, 1H), 1.69-1.45 (m, 4H), 1.30-1.24 (m, 2H), 1.12 (br s, 1H); ES+ MS: 459 (M+1).
Sources & evidence
- ORD record
- ord-b0d609ecb28642a497738ae6bc685232
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08129385B2
Reaction notes
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