Formaldehyde → HCID 44242442, compound

HRID 1775949Notes

Reaction equation

HRID 1775949 reaction equation
Cl.Cl[C:3]1C=CC(NN)=CC=1.BrCCN1CCN(C(OC(C)(C)C)=O)CC1.C(OC(OCC)CCCNC)C.[Cl:39][C:40]1[CH:41]=[C:42]2[C:46](=[CH:47][CH:48]=1)[N:45]([CH2:49][CH2:50][N:51]1[CH2:56][CH2:55][N:54](C(OC(C)(C)C)=O)[CH2:53][CH2:52]1)[CH:44]=[C:43]2[CH2:64][CH2:65][NH:66][CH3:67].C=O.C(O)(C(F)(F)F)=O.C(O)(C(F)(F)F)=O.ClCCl>C(#N)C.C(N(CC)CC)C>[Cl:39][C:40]1[CH:48]=[C:47]2[C:46](=[CH:42][CH:41]=1)[N:45]([CH2:49][CH2:50][N:51]1[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]1)[C:44]1[CH2:3][N:66]([CH3:67])[CH2:65][CH2:64][C:43]2=1

Participants

10

Reactant 7

HCID 712FormaldehydeHCID 6422Trifluoroacetic acidHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 139945474,4-Diethoxy-N-methylbutan-1-amineHCID 15946441tert-Butyl 4-(2-bromoethyl)piperazine-1-carboxylateHCID 21863450Trifluoroacetic acid methylene chlorideHCID 66911717HCID 66911717, compound

Product 1

HCID 44242442HCID 44242442, compound

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, tert-butyl 4-(2-bromoethyl)piperazine-1-carboxylate, and triethylamine (General Method 1), N-Boc-1-(4-chlorophenyl)-1-(2-(piperazin-1-yl)ethyl)hydrazine and 4,4-diethoxy-N-methylbutan-1-amine (General Method 3), tert-butyl 4-(2-(5-chloro-3-(2-(methylamino)ethyl)-1H-indol-1-yl)ethyl)piperazine-1-carboxylate, formaldehyde and TFA in acetonitrile (General Method 4), and Boc deprotection by using TFA/dichloromethane.

Sources & evidence

ORD record
ord-2debe482041049dfa92ef3b3207bad86
Source dataset
uspto-grants-2016_02
Patent number
US09260429B2

Reaction notes

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