Formaldehyde → 6-chloro-2,3,4,9-tetrahydro-2-methyl-9-(2-(2-methylpyrimidin-5-yl)ethyl)-1H-pyrido[3,4-b]indole

HRID 2198295Notes

Reaction equation

HRID 2198295 reaction equation
Cl.Cl[C:3]1C=CC(NN)=CC=1.BrCCC1C=NC(C)=NC=1.C(OC(OCC)CCCNC)C.[Cl:33][C:34]1[CH:35]=[C:36]2[C:40](=[CH:41][CH:42]=1)[N:39]([CH2:43][CH2:44][C:45]1[CH:46]=[N:47][C:48]([CH3:51])=[N:49][CH:50]=1)[CH:38]=[C:37]2[CH2:52][CH2:53][NH:54][CH3:55].C=O.C(O)(C(F)(F)F)=O>C(#N)C.C(N(CC)CC)C>[Cl:33][C:34]1[CH:35]=[C:36]2[C:40](=[CH:41][CH:42]=1)[N:39]([CH2:43][CH2:44][C:45]1[CH:50]=[N:49][C:48]([CH3:51])=[N:47][CH:46]=1)[C:38]1[CH2:55][N:54]([CH3:3])[CH2:53][CH2:52][C:37]2=1

Participants

9

Reactant 6

HCID 712FormaldehydeHCID 6422Trifluoroacetic acidHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 139945474,4-Diethoxy-N-methylbutan-1-amineHCID 669117205-(2-Bromoethyl)-2-methylpyrimidineHCID 669117812-(5-chloro-1-(2-(2-methylpyrimidin-5-yl)ethyl)-1H-indol-3-yl)-N-methylethanamine

Product 1

HCID 442421776-chloro-2,3,4,9-tetrahydro-2-methyl-9-(2-(2-methylpyrimidin-5-yl)ethyl)-1H-pyrido[3,4-b]indole

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

The title compound is prepared by following General Methods 1, 3 and 4 using 4-chlorophenylhydrazine hydrochloride, 5-(2-bromoethyl)-2-methylpyrimidine, and triethylamine (General Method 1), 3,1-(4-chlorophenyl)-1-(2-(2-methylpyrimidin-5-yl)ethyl)hydrazine (Example 1) and 4,4-diethoxy-N-methylbutan-1-amine (General Method 3) and 2-(5-chloro-1-(2-(2-methylpyrimidin-5-yl)ethyl)-1H-indol-3-yl)-N-methylethanamine (Example 10), formaldehyde and TFA in acetonitrile (General Method 4).

Sources & evidence

ORD record
ord-3299044a7de9434892120250d4b0e709
Source dataset
uspto-grants-2012_12
Patent number
US08338447B2

Reaction notes

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