5-methyl 1-(4-nitrophenyl) (6S)-6-(3,4-difluorophenyl)-4-(methoxymethyl)-2-oxo-3,6-dihydro-1,5(2H)-pyrimidinedicarboxylate → methyl (4S)-3-({[3-(4-[3-(acetylamino)phenyl]-3,6-dihydro-1(2H)-pyridinyl)propyl]amino}carbonyl)-4-(3,4-difluorophenyl)-6-(methoxymethyl)-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[N:14]([C:15](OC3C=CC([N+]([O-])=O)=CC=3)=[O:16])[C:13](=[O:27])[NH:12][C:11]([CH2:28][O:29][CH3:30])=[C:10]2[C:31]([O:33][CH3:34])=[O:32])[CH:5]=[CH:6][C:7]=1[F:8].[NH2:35][CH2:36][CH2:37][CH2:38][N:39]1[CH2:44][CH:43]=[C:42]([C:45]2[CH:46]=[C:47]([NH:51][C:52](=[O:54])[CH3:53])[CH:48]=[CH:49][CH:50]=2)[CH2:41][CH2:40]1>>[C:52]([NH:51][C:47]1[CH:46]=[C:45]([C:42]2[CH2:43][CH2:44][N:39]([CH2:38][CH2:37][CH2:36][NH:35][C:15]([N:14]3[C@@H:9]([C:4]4[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=4)[C:10]([C:31]([O:33][CH3:34])=[O:32])=[C:11]([CH2:28][O:29][CH3:30])[NH:12][C:13]3=[O:27])=[O:16])[CH2:40][CH:41]=2)[CH:50]=[CH:49][CH:48]=1)(=[O:54])[CH3:53]Participants
3
Reactant 2
Product 1
Procedure
Prepared from the reaction of 5-methyl 1-(4-nitrophenyl) (6S)-6-(3,4-difluorophenyl)-4-(methoxymethyl)-2-oxo-3,6-dihydro-1,5(2H)-pyrimidinedicarboxylate (describe in PCT Publication No. WO 00/37026, published Jun. 29, 2000) and N-{3-[1-(3-aminopropyl)-1,2,3,6-tetrahydro-4-pyridinyl]phenyl}acetamide: 1H NMR δ 8.90 (t, 1H, J=3.6 Hz), 7.75 (s, 1H), 7.50-7.00 (m, 8H), 6.68 (s, 1H), 6.03 (br s, 1H), 4.67 (s, 2H), 3.71 (s, 3H), 3.47 (s, 3H), 3.38 (ABm, 2H), 3.16 (m, 2H), 2.71 (t, 2H, J=5.4 Hz), 2.56 (m, 4H), 2.35-1.90 (br, 2H), 2.17 (s, 3H), 1.82 (p, 2H, J=7.2 Hz); ESMS, 612.25 (M+H)+.
Sources & evidence
- ORD record
- ord-878a03f1c9e64597bc66d8d8a0f09be8
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07473698B2
Reaction notes
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