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

HRID 1775920Notes

Reaction equation

HRID 1775920 reaction equation
Cl.ClC1C=CC(NN)=CC=1.BrCCC1C=NC(C(F)(F)F)=NC=1.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]([CH2:33][CH2:34][C:35]2[CH:36]=[N:37][C:38]([C:41]([F:44])([F:43])[F:42])=[N:39][CH:40]=2)N)=[CH:27][CH:26]=1.C(OC(OCC)CCCNC)C.ClC1C=C2[C:64](=CC=1)[N:63]([CH2:67][CH2:68][C:69]1[CH:70]=NC(C(F)(F)F)=NC=1)[CH:62]=C2CCNC.C=O.C(O)(C(F)(F)F)=O>C(#N)C.C(N(CC)CC)C>[Cl:24][C:25]1[CH:30]=[C:29]2[C:28](=[CH:27][CH:26]=1)[N:31]([CH2:33][CH2:34][C:35]1[CH:36]=[N:37][C:38]([C:41]([F:44])([F:43])[F:42])=[N:39][CH:40]=1)[C:70]1[CH2:64][N:63]([CH3:62])[CH2:67][CH2:68][C:69]2=1

Participants

10

Reactant 7

HCID 712FormaldehydeHCID 6422Trifluoroacetic acidHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 139945474,4-Diethoxy-N-methylbutan-1-amineHCID 66911660Pyrimidine, 5-(2-bromoethyl)-2-(trifluoromethyl)-HCID 669117132-(5-chloro-1-(2-(2-(trifluoromethyl)pyrimidin-5-yl)ethyl)-1H-indol-3-yl)-N-methylethanamineHCID 669117331-(4-Chlorophenyl)-1-(2-(2-(trifluoromethyl)pyrimidin-5-yl)ethyl)hydrazine

Product 1

HCID 579304486-chloro-9-(2-(2-(trifluoromethyl)pyrimidin-5-yl)ethyl)-2,3,4,9-tetrahydro-2-methyl-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-(trifluoromethyl)pyrimidine, and triethylamine (General Method 1), 1-(4-chlorophenyl)-1-(2-(2-(trifluoromethyl)pyrimidin-5-yl)ethyl)hydrazine and 4,4-diethoxy-N-methylbutan-1-amine (General Method 3) and 2-(5-chloro-1-(2-(2-(trifluoromethyl)pyrimidin-5-yl)ethyl)-1H-indol-3-yl)-N-methylethanamine, formaldehyde and TFA in acetonitrile (General Method 4).

Sources & evidence

ORD record
ord-45a1425423dc4bbf9bcef118398ce727
Source dataset
uspto-grants-2016_02
Patent number
US09260429B2

Reaction notes

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