9-ethyl-8-iodo-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile → 9-Ethyl-8-(4-hydroxy-piperidin-1-yl)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile
Reaction equation
C(C1C(I)=CC2C(C)(C)C3NC4C(C=3C(=O)C=2C=1)=CC=C(C#N)C=4)C.[CH2:26]([C:28]1[C:49]([N:50]2[CH2:55][CH2:54][C:53](=[O:56])[CH2:52][CH2:51]2)=[CH:48][C:31]2[C:32]([CH3:47])([CH3:46])[C:33]3[NH:34][C:35]4[C:40]([C:41]=3[C:42](=[O:43])[C:30]=2[CH:29]=1)=[CH:39][CH:38]=[C:37]([C:44]#[N:45])[CH:36]=4)[CH3:27]>>[CH2:26]([C:28]1[C:49]([N:50]2[CH2:51][CH2:52][CH:53]([OH:56])[CH2:54][CH2:55]2)=[CH:48][C:31]2[C:32]([CH3:47])([CH3:46])[C:33]3[NH:34][C:35]4[C:40]([C:41]=3[C:42](=[O:43])[C:30]=2[CH:29]=1)=[CH:39][CH:38]=[C:37]([C:44]#[N:45])[CH:36]=4)[CH3:27]Participants
Reactant 2
Product 1
Procedure
The compounds described in the following Tables 8-10 were synthesized by introducing a corresponding amine to 9-ethyl-6,6-dimethyl-8-iodo-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile according to the method used for the synthesis of Compound PR9-1. Although the relevant literatures are not entirely known, some amines in which a tertiary alkyl group is attached to the nitrogen atom were prepared according to the method described in Journal of Medicinal Chemistry, 45 (14), 3143-3160, 2002. Alternatively, the preparation was carried out by introducing a corresponding amine to 9-ethyl-6,6-dimethyl-11-oxo-8-(4-oxopiperidin-1-yl)-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile based on the method that is used for the synthesis of Compound PR11-1 (i.e., reductive amination).
Workup
- customwere synthesized
- customused for the synthesis of Compound PR9-1
- customwere prepared
- customis used for the synthesis of Compound PR11-1 (i.e., reductive amination)
Sources & evidence
- ORD record
- ord-28b5830e95654dc69841faa7001b7a87
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09440922B2
Reaction notes
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