Formaldehyde → HCID 44242574, compound
Reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH:9]N)[CH:6]=[CH:7][CH:8]=1.BrCC([O:15][CH2:16][CH3:17])=O.Cl[C:19]1[CH:20]=[C:21]([N:25]([CH2:27]C(OCC)=O)N)C=[CH:23][CH:24]=1.C(O[CH:36](OCC)[CH2:37][CH2:38][CH2:39][NH:40][CH3:41])C.ClC1C=C2C(C(CCNC)=CN2CC(OCC)=O)=CC=1.C=O.C(O)(C(F)(F)F)=O.ClC1C=C2C(C3CCN(C)CC=3N2CC(O)=O)=CC=1.N1CCCCC1.CCN=C=NCCCN(C)C>C(#N)C.ClC1C=C2C(C3CCN(C)CC=3N2CC(OCC)=O)=CC=1.[OH-].[Na+].C(N(CC)CC)C>[Cl:2][C:3]1[CH:4]=[C:5]2[C:6]([C:19]3[CH2:24][CH2:23][N:25]([CH3:27])[CH2:21][C:20]=3[N:9]2[CH2:17][C:16]([N:40]2[CH2:41][CH2:36][CH2:37][CH2:38][CH2:39]2)=[O:15])=[CH:7][CH:8]=1Participants
15
Reactant 10
HCID 712Formaldehyde
HCID 6422Trifluoroacetic acid
HCID 7748Ethyl bromoacetate
HCID 8082Piperidine
HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide
HCID 75331m-Chlorophenylhydrazine hydrochloride
HCID 139945474,4-Diethoxy-N-methylbutan-1-amine
HCID 66911678HCID 66911678, compound
HCID 66911687HCID 66911687, compound
HCID 66911765HCID 66911765, compoundProduct 1
Reagents, catalysts & solvents 4
Procedure
The title compound is prepared by following General Methods 1, 3, 4, 5 and 7 by using 3-chlorophenylhydrazine hydrochloride, ethyl bromoacetate, and triethylamine (General Method 1), ethyl 2-(1-(3-chlorophenyl)hydrazinyl)acetate and 4,4-diethoxy-N-methylbutan-1-amine (General Method 3), ethyl 2-(6-chloro-3-(2-(methylamino)ethyl)-1H-indol-1-yl)acetate, formaldehyde and TFA in acetonitrile (General Method 4), ethyl 2-(7-chloro-1,2,3,4-tetrahydro-2-methylpyrido[3,4-b]indol-9-yl)acetate and NaOH (General Method 5), and 2-(7-chloro-1,2,3,4-tetrahydro-2-methylpyrido[3,4-b]indol-9-yl)acetic acid, piperidine and EDCI (General Method 7).
Sources & evidence
- ORD record
- ord-00e74d246720464d8768951cd12716d7
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08338447B2
Reaction notes
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