Dichloroacetic Acid → HCID 20079371, compound

HRID 1654075Notes

Reaction equation

HRID 1654075 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[NH:13][C:12]1[CH2:15][N:16]([CH2:19][C:20]([NH:22][CH:23]([CH:30]([CH3:32])[CH3:31])[CH:24]([OH:29])[C:25]([F:28])([F:27])[F:26])=[O:21])[CH:17]=[CH:18][C:11]2=1)=[O:5])[CH3:2].Cl.CN(C)CCCN=C=NCC.ClC(Cl)C(O)=O.C(OCC)(=O)C>CS(C)=O.C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[NH:13][C:12]1[CH2:15][N:16]([CH2:19][C:20]([NH:22][CH:23]([CH:30]([CH3:31])[CH3:32])[C:24](=[O:29])[C:25]([F:28])([F:26])[F:27])=[O:21])[CH:17]=[CH:18][C:11]2=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 6597Dichloroacetic AcidHCID 8857Ethyl AcetateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 20079376HCID 20079376, compound

Product 1

HCID 20079371HCID 20079371, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 1140TolueneSolvent

Procedure

To a solution of 2-(8-ethoxycarbonyl-1,2-dihydropyrido[3,4-b]indol-2-yl)-N-(3,3,3-trifluoro-2-hydroxy-1-isopropylpropyl)acetamide (0.57 g) in dimethyl sulfoxide (6 mL) and toluene (6 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.3 g) and dichloroacetic acid (0.43 mL) and the resulting solution allowed to stir for 2 hours. The reaction mixture was poured into ethyl acetate, washed (1N hydrochloric acid, H2O), dried, and evaporated. The resulting material was purified by chromatography, with methanol:dichloromethane (3:97) as the eluent. The resulting solid was recrystallized from ethyl acetate to give the title compound (0.41 g); mp 218°-219° C.

Workup

  1. washwashed (1N hydrochloric acid, H2O)
  2. customdried
  3. customevaporated
  4. customThe resulting material was purified by chromatography, with methanol:dichloromethane (3:97) as the eluent
  5. customThe resulting solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-5af6553161a34d6ab02d4a072f7382b4
Source dataset
uspto-grants-1995_04
Patent number
US05405852

Reaction notes

Loading…