Acetic Acid → HCID 16113775, compound

HRID 2245512Notes

Reaction equation

HRID 2245512 reaction equation
N([C:3]([CH:5]([N:13]1[C:21]2[C:16](=[CH:17][C:18]([NH:22][S:23]([C:26]3[CH:31]=[CH:30][C:29]([O:32][C:33]([F:36])([F:35])[F:34])=[CH:28][CH:27]=3)(=[O:25])=[O:24])=[CH:19][CH:20]=2)[CH:15]=[CH:14]1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4])N.Cl.C(O)(=[O:40])C>>[C:7]1([CH2:6][CH:5]([N:13]2[C:21]3[C:16](=[CH:17][C:18]([NH:22][S:23]([C:26]4[CH:31]=[CH:30][C:29]([O:32][C:33]([F:34])([F:35])[F:36])=[CH:28][CH:27]=4)(=[O:24])=[O:25])=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)[C:3]([OH:40])=[O:4])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 16113986HCID 16113986, compound

Product 1

HCID 16113775HCID 16113775, compound

Conditions

Temperature
80 °C

Procedure

To N-[1-(1-hydrazinocarbonyl-2-phenyl-ethyl)-1H-indol-5-yl]-4-trifluoro methoxy-benzenesulfonamide (0.07 g, 0.13 mmol) in acetic acid at ambient temperature under a laboratory atmosphere was added conc. HCl (1 ml) then the reaction vessel was capped. The dark red mixture was heated at 80° C. for 15 hours (the vessel was periodically uncapped then recapped to release pressure build up with in the vessel). The reaction was cooled to ambient temperature and concentrated in vacuo to a dark red powder. The crude product was subjected to gradient RP-HPLC (H2O: CH3CN) and the title compound was isolated as a red powder (0.06 g, 91% yield): MS (ESI) m/z 505, MS (ESI) m/z 503.

Workup

  1. customthe reaction vessel was capped
  2. temperatureThe reaction was cooled to ambient temperature
  3. concentrationconcentrated in vacuo to a dark red powder

Sources & evidence

ORD record
ord-e34db12ea501489abf5c94fef1c09094
Source dataset
uspto-grants-2010_03
Patent number
US07683091B2

Reaction notes

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