Dichloroacetic Acid → HCID 9827187, compound

HRID 1654072Notes

Reaction equation

HRID 1654072 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]1[C:12](=[O:36])[N:13]([CH2:22][C:23]([NH:25][CH:26]([CH:33]([CH3:35])[CH3:34])[CH:27]([OH:32])[C:28]([F:31])([F:30])[F:29])=[O:24])[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:15][C:8]2=1)=[O:2].Cl.CN(C)CCCN=C=NCC.ClC(Cl)C(O)=O.C(OCC)(=O)C>CS(C)=O.C1(C)C=CC=CC=1>[CH:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]1[C:12](=[O:36])[N:13]([CH2:22][C:23]([NH:25][CH:26]([CH:33]([CH3:34])[CH3:35])[C:27](=[O:32])[C:28]([F:29])([F:30])[F:31])=[O:24])[C:14]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:15][C:8]2=1)=[O:2]

Participants

7

Reactant 4

HCID 6597Dichloroacetic AcidHCID 8857Ethyl AcetateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10368669HCID 10368669, compound

Product 1

HCID 9827187HCID 9827187, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 1140TolueneSolvent

Procedure

To a solution of 2-(8-formyl-1-oxo-3-phenyl-1,2-dihydropyrido[3,4-b]indol-2-yl)-N-(3,3,3-trifluoro-2-hydroxy-1-isopropylpropyl)acetamide (0.1 g) in dimethylsulfoxide (1 mL) and toluene (1 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.46 g) and dichloroacetic acid (0.I mL). The resulting solution was allowed to stir for 2 hours. The mixture was poured into ethyl acetate, washed (1N hydrochloric acid, H2O), dried, and evaporated. The resulting material was chromatographed, with ether:ethyl acetate (gradient, 1:1, 0:1) as the eluent, to give the title compound (0.1 g) as a white solid; TLC: Rf =0.5, methanol:dichloromethane (5:95); 300 MHz.

Workup

  1. washwashed (1N hydrochloric acid, H2O)
  2. customdried
  3. customevaporated
  4. customThe resulting material was chromatographed, with ether

Sources & evidence

ORD record
ord-146f5ba3a7f94c18a2e521d1f8a667bd
Source dataset
uspto-grants-1995_04
Patent number
US05405852

Reaction notes

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