Formaldehyde → HCID 44242508, compound

HRID 2198335Notes

Reaction equation

HRID 2198335 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.BrCC([O:15][CH2:16][CH3:17])=O.Cl[C:19]1[CH:24]=C[C:22]([N:25]([CH2:27]C(OCC)=O)N)=[CH:21][CH:20]=1.C(OC(OCC)CCCNC)C.ClC1C=C2C(=CC=1)N(CC(OCC)=O)C=C2CCNC.C=O.C(O)(C(F)(F)F)=O.ClC1C=C2C(=CC=1)[N:80](CC(O)=O)[C:79]1[CH2:88][N:89]([CH3:92])[CH2:90][CH2:91]C2=1.CN1CCNCC1.CCN=C=NCCCN(C)C>C(#N)C.ClC1C=C2C(=CC=1)N(CC(OCC)=O)C1CN(C)CCC2=1.[OH-].[Na+].C(N(CC)CC)C>[Cl:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][CH:4]=1)[N:9]([CH2:17][C:16]([N:80]1[CH2:79][CH2:88][N:89]([CH3:92])[CH2:90][CH2:91]1)=[O:15])[C:21]1[CH2:22][N:25]([CH3:27])[CH2:24][CH2:19][C:20]2=1

Participants

15

Reactant 10

HCID 712FormaldehydeHCID 6422Trifluoroacetic acidHCID 7748Ethyl bromoacetateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 531671-MethylpiperazineHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 139945474,4-Diethoxy-N-methylbutan-1-amineHCID 44242581HCID 44242581, compoundHCID 57930382HCID 57930382, compoundHCID 57930384HCID 57930384, compound

Product 1

HCID 44242508HCID 44242508, compound

Reagents, catalysts & solvents 4

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolventHCID 14798Sodium HydroxideSolventHCID 57930381HCID 57930381, compoundSolvent

Procedure

The title compound is prepared by following General Methods 1, 3, 4, 5 and 7 by using 4-chlorophenylhydrazine hydrochloride, ethyl bromoacetate, and triethylamine (General Method 1), ethyl 2-(1-(4-chlorophenyl)hydrazinyl)acetate and 4,4-diethoxy-N-methylbutan-1-amine (General Method 3), ethyl 2-(5-chloro-3-(2-(methylamino)ethyl)-1H-indol-1-yl)acetate, formaldehyde and TFA in acetonitrile (General Method 4), ethyl 2-(6-chloro-1,2,3,4-tetrahydro-2-methylpyrido[3,4-b]indol-9-yl)acetate and NaOH (General Method 5), and 2-(6-chloro-1,2,3,4-tetrahydro-2-methylpyrido[3,4-b]indol-9-yl)acetic acid, N-methylpiperazine and EDCI (General Method 7).

Sources & evidence

ORD record
ord-ccac1ce9f2b04660b08dee407815d15d
Source dataset
uspto-grants-2012_12
Patent number
US08338447B2

Reaction notes

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