Ethanol → HCID 178457088, compound

HRID 1189667Notes

Reaction equation

HRID 1189667 reaction equation
[F:1][C:2]([F:29])([F:28])[C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10](=[O:27])[C:11]2[CH:16]=[C:15]([N+:17]([O-])=O)[C:14]([NH:20][CH3:21])=[CH:13][C:12]=2[N:22]([CH3:26])[CH2:23][C:24]#[CH:25])[CH2:5][CH2:4]1.[O-]S(S([O-])=O)=O.[Na+].[Na+].O.CCO>C([O-])(O)=O.[Na+]>[F:1][C:2]([F:28])([F:29])[C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10](=[O:27])[C:11]2[CH:16]=[C:15]([NH2:17])[C:14]([NH:20][CH3:21])=[CH:13][C:12]=2[N:22]([CH3:26])[CH2:23][C:24]#[CH:25])[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 24489Sodium DithioniteHCID 178457089HCID 178457089, compound

Product 1

HCID 178457088HCID 178457088, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of N-(trans-4-trifluoromethyl-cyclohexyl)-2-[N-methyl-N-propargylamino]-4-methylamino-5-nitro-benzoic acid amide (60 mg, 0.145 mmol), Na2S2O4 (127 mg and a second 150 mg portion is added after 8 h), 1 mL water and 5 mL EtOH is stirred at 55° C. for 24 h. The mixture is diluted with sat aq NaHCO3 and extracted with EtOAc. The combined organic phases are dried with Na2SO4, filtered and concentrated.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic phases are dried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cf781453221e4dba93c905e764772c02
Source dataset
uspto-grants-2014_03
Patent number
US08674113B2

Reaction notes

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