Piperidine carboxylate → 1-({2-[(1S,2S)-2-Hydroxycyclohexyl]-3-oxo-2,3-dihydro-1H-benzo[e]isoindol-5-yl}methyl)-4-(6-methoxypyridin-2-yl)piperidine-4-carbonitrile
Reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[N:8]1[CH2:16][C:15]23[CH:17]=[CH:18][CH:19]=[CH:20][C:14]2=[CH:13][C:12]([CH2:21][N:22]2[CH2:27][CH2:26][C:25]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=4)([C:28]#[N:29])[CH2:24][CH2:23]2)=[CH:11][CH:10]3[C:9]1=[O:36].N1([C:43]([O-])=[O:44])CCCCC1.C(C1(C2C=CC=CN=2)CCN(C(OC(C)(C)C)=O)CC1)#N>>[OH:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[N:8]1[CH2:16][C:15]2[C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=3[C:12]([CH2:21][N:22]3[CH2:27][CH2:26][C:25]([C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([O:44][CH3:43])[N:31]=4)([C:28]#[N:29])[CH2:24][CH2:23]3)=[CH:11][C:10]=2[C:9]1=[O:36]Participants
Reactant 3
Product 1
Procedure
The titled compound was prepared employing the procedures described for the construction of 1-({2-[(1S,2S)-2-hydroxycyclohexyl]-3-oxo-2,3-dihydro-1H-benzo[d]isoindol-5-yl}methyl)-4-(pyridine-2-yl)piperidine-4-carbonitrile in Example 1, substituting tert-butyl 4-cyano-4-methoxypyridin-2-yl)piperidine-1-carboxylate for tert-butyl 4-cyano-4-pyridin-2-ylpiperidine-1-carboxylate. The resultant white solid gave proton NMR spectra consistent with theory and a mass ion (ES+) of 511.2715 for [M+H]+[calc'd for C31H35N4O3, [M+H]+=511.2704]: 1H NMR (400 MHz, CDCl3) δ 8.19-8.11 (m, 2H), 7.90-7.83 (m, 2H), 7.68 (s, 1H), 7.67-7.52 (m, 3H), 5.04-4.92 (m, 2H), 4.59-4.54 (m, 2H), 4.17-4.11 (m, 2H), 3.78-3.71 (m, 2H), 2.23-2.19 (m, 2H), 1.96-1.81 (m, 4H), 1.64-1.20 (m, 1H) ppm.
Workup
- customThe resultant white solid gave proton NMR spectra consistent with theory
Sources & evidence
- ORD record
- ord-c4f9d86f40be4257a38c1ecd197e32fc
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09206200B2
Reaction notes
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