Toluene → HCID 10391720, compound

HRID 1654074Notes

Reaction equation

HRID 1654074 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:13]=1[NH:12][C:11]1[C:14](=[O:38])[N:15]([CH2:24][C:25]([NH:27][CH:28]([CH:35]([CH3:37])[CH3:36])[C:29](=[O:34])[C:30]([F:33])([F:32])[F:31])=[O:26])[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:17][C:10]2=1)=[O:4].C1(C)C=CC=CC=1.ClC(Cl)C(O)=O.C(OCC)(=O)C>CS(C)=O>[C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:13]=1[NH:12][C:11]1[C:14](=[O:38])[N:15]([CH2:24][C:25]([NH:27][CH:28]([CH:35]([CH3:36])[CH3:37])[C:29](=[O:34])[C:30]([F:32])([F:33])[F:31])=[O:26])[C:16]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[CH:17][C:10]2=1)([OH:4])=[O:2]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6597Dichloroacetic AcidHCID 8857Ethyl AcetateHCID 10052622HCID 10052622, compound

Product 1

HCID 10391720HCID 10391720, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-(8-Methoxycarbonyl-1-oxo-3-phenyl-1,2-dihydropyrido[3,4-b]-indol-2-yl)-N-(3,3,3-trifluoro-1-isopropyl-2-oxopropyl)acetamide. To a solution of the product from Example 3.a. (0.1 g) in dimethyl sulfoxide (1 mL) and toluene (1 mL) was added 1-(3-dimethyl- aminopropyl)-3-ethylcarbodiimide hydrochloride (0.34 g) and dichloroacetic acid (0.06 mL), and 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 as the eluent, give the ketone (0.90 g) as a white solid; TLC: Rf =0.65, methanol:dichloromethane (2:98); MS: m/z=528(M+1).

Workup

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

Sources & evidence

ORD record
ord-a8c459e0d2494524be45118a6bb61fcc
Source dataset
uspto-grants-1995_04
Patent number
US05405852

Reaction notes

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