Formaldehyde → 2-(7-chloro-2-methyl-3,4-dihydro-1H-pyrido[3,4-b]indol-9(2H)-yl)-1-(6-methylpyridin-3-yl)ethanol

HRID 1775917Notes

Reaction equation

HRID 1775917 reaction equation
Cl.Cl[C:3]1[CH:4]=[C:5]([NH:9]N)[CH:6]=[CH:7][CH:8]=1.[CH2:11]([O:13]C(OCC)CCCNC)[CH3:12].[Cl:23][C:24]1[CH:32]=[C:31]2[C:27]([C:28]([CH2:33][CH2:34][NH:35][CH3:36])=[CH:29][NH:30]2)=[CH:26][CH:25]=1.C=O.[C:39](O)(C(F)(F)F)=O>C(#N)C.ClC1C=C2C(C3CCN(C)CC=3N2)=CC=1.CC1C=CC(C2CO2)=CN=1.[H-].[Na+]>[Cl:23][C:24]1[CH:32]=[C:31]2[C:27]([C:28]3[CH2:33][CH2:34][N:35]([CH3:39])[CH2:36][C:29]=3[N:30]2[CH2:12][CH:11]([C:4]2[CH:5]=[N:9][C:7]([CH3:6])=[CH:8][CH:3]=2)[OH:13])=[CH:26][CH:25]=1

Participants

10

Reactant 5

HCID 712FormaldehydeHCID 6422Trifluoroacetic acidHCID 75331m-Chlorophenylhydrazine hydrochlorideHCID 139945474,4-Diethoxy-N-methylbutan-1-amineHCID 21071655[2-(6-Chloro-1h-indol-3-yl)ethyl](methyl)amine

Product 1

HCID 442421802-(7-chloro-2-methyl-3,4-dihydro-1H-pyrido[3,4-b]indol-9(2H)-yl)-1-(6-methylpyridin-3-yl)ethanol

Reagents, catalysts & solvents 4

HCID 6342AcetonitrileSolventHCID 24758Sodium hydrideSolventHCID 157135882-Methyl-5-(oxiran-2-yl)pyridineSolventHCID 579304787-chloro-2-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indoleSolvent

Procedure

The title compound is prepared by following General Methods 3, 4 and 8 by using 3-chlorophenylhydrazine hydrochloride and 4,4-diethoxy-N-methylbutan-1-amine (General Method 3), 2-(6-chloro-1H-indol-3-yl)-N-methylethanamine, formaldehyde and TFA in acetonitrile (General Method 4) and 7-chloro-2,3,4,9-tetrahydro-2-methyl-1H-pyrido[3,4-b]indole, 2-methyl-5-(oxiran-2-yl)pyridine and NaH (General Method 8).

Sources & evidence

ORD record
ord-fbb606610dc6429b864e1308942ab289
Source dataset
uspto-grants-2016_02
Patent number
US09260429B2

Reaction notes

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