Sodium Azide → HCID 25142484, compound

HRID 1987795Notes

Reaction equation

HRID 1987795 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]3([CH:16]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[CH:18]=4)[CH2:15][C:14](=[O:24])[CH2:13][CH:12]3[C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[N-:32]=[N+]=[N-].[Na+]>C(#N)C.Cl[Ti](Cl)(Cl)Cl>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C@:6]3([C@@H:16]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[CH:18]=4)[CH2:15][C:14](=[O:24])[NH:32][CH2:13][C@H:12]3[C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 67213015HCID 67213015, compound

Product 1

HCID 25142484HCID 25142484, compoundYield 7.8%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

In a manner similar to the method described in example 2 (method A), rac-(1R,2S,6R)-6′-chloro-2-(3-chlorophenyl)-6-(3-methylphenyl)spiro[cyclohexane-1,3′-[3H]indole]-2′,4(1′H)-dione (140 mg, 0.31 mmol) was reacted with NaN3 (50.1 mg, 0.78 mmole) in the presence of TiCl4 (1.0 M in CH2Cl2, 0.31 mL) (Aldrich) in acetonitrile (10 mL) followed by chiral chromatograph to give (3S,4R,5R)-6′-chloro-3-(3-chlorophenyl)-1,1′,2,2′,3,5,6,7-octahydro-5-(3-methylphenyl)-spiro[4H-azepine-4,3′-[3H]-indole]-2′,7-dione (11.2 mg): HRMS (ES+) m/z Calcd for C26H22Cl2N2O2+H [(M+H)+]: 465.1131. Found: 465.1132; (3S,4R,5R)-6′-chloro-5-(3-chlorophenyl)-1,1′,2,2′,3,5,6,7-octahydro-3-(3-methylphenyl)-spiro[4H-azepine-4,3′-[3H]-indole]-2′,7-dione (10.7 mg): HRMS (ES+) m/z Calcd for C26H22Cl2N2O2+H [(M+H)+]: 465.1131. Found: 465.1131; (3R,4S,5S)-6′-chloro-3-(3-chlorophenyl)-1,1′,2,2′,3,5,6,7-octahydro-5-(3-methylphenyl)-spiro[4H-azepine-4,3′-[3H]-indole]-2′,7-dione (10.3 mg): HRMS (ES+) m/z Calcd for C26H22Cl2N2O2+H [(M+H)+]: 465.1131. Found: 465.1131; and (3R,4S,5S)-6′-chloro-5-(3-chlorophenyl)-1,1′,2,2′,3,5,6,7-octahydro-3-(3-methylphenyl)-spiro[4H-azepine-4,3′-[3H]-indole]-2′,7-dione (10.1 mg): HRMS (ES+) m/z Calcd for C26H22Cl2N2O2+H [(M+H)+]: 465.1131. Found: 465.1131.

Sources & evidence

ORD record
ord-8988bfb87d364a789ad86c8fa3d85e30
Source dataset
uspto-grants-2009_06
Patent number
US07553833B2

Reaction notes

Loading…