HCID 21952613, compound → (4aS,9bR)-8-(2-isopropoxy-pyridin-3-ylamino)-5-methyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole-6-carbonitrile
Reaction equation
CN1C2C(C(F)(F)F)=CC(NC3C=NC=CC=3)=CC=2C2CNCCC12.[CH3:26][N:27]1[C:35]2[C:30](=[CH:31][C:32]([NH:38][C:39]3[CH:40]=[N:41][CH:42]=[CH:43][C:44]=3C(F)(F)F)=[CH:33][C:34]=2[C:36]#[N:37])[C@@H:29]2[CH2:49][NH:50][CH2:51][CH2:52][C@H:28]12.BrC1C([O:60][CH:61]([CH3:63])[CH3:62])=NC=CC=1.CC([O-])(C)C.[Na+]>>[CH:61]([O:60][C:40]1[C:39]([NH:38][C:32]2[CH:31]=[C:30]3[C:35](=[C:34]([C:36]#[N:37])[CH:33]=2)[N:27]([CH3:26])[C@H:28]2[CH2:52][CH2:51][NH:50][CH2:49][C@@H:29]32)=[CH:44][CH:43]=[CH:42][N:41]=1)([CH3:63])[CH3:62]Participants
Reactant 4
Product 1
Procedure
The title compound was prepared by following the general method for (5-methyl-6-trifluoromethyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indol-8-yl)-pyridin-3-yl-amine (Method B) as a tan solid (32 mg, 21%) from (4aS,9bR)-8-amino-6-cyano-3,4,4a,9b-tetrahydro-1H-pyrido[4,3-b]indole-2,5-dicarboxylic acid tert-butyl ester (Example 162, 150 mg, 0.46 mmol), 3-bromo-2-iso-propoxypyridine (91 mg, 0.42 mmol) and NaOt-Bu (66 mg, 0.69 mmol). 1H NMR (300 MHz, CDCl3) δ 7.58 (dd, J=5.0, 1.4 Hz, 1H), 7.18–6.97 (m, 3H), 6.71 (dd, J=7.6, 5.0 Hz, 1H), 5.83 (br s, 1H), 5.41 (sept, J=6.2 Hz, 1H), 3.53–3.48 (m, 1H), 3.33–3.01 (m, 4H), 2.99–2.80 (m, 2H), 2.79–2.61 (m, 1H), 2.59–2.01 (m, 1H), 2.00–1.80 (m, 2H), 1.39 (d, J=6.2 Hz, 6H); APCI MS m/z 364 [C21H25N5O+H]+.
Sources & evidence
- ORD record
- ord-9fe519732e1e441eb6b2ba1b513e416d
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07109339B2
Reaction notes
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