Hydrochloric Acid → HCID 57812454, compound

HRID 911980Notes

Reaction equation

HRID 911980 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[C:4]([Cl:10])[C:3]=1[CH:11]([O:13][C:14]1[C:15]2[O:25][CH:24]=[C:23]([C:26]3[CH:27]=[N:28][N:29]([CH:31]4[CH2:36][CH2:35][N:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:33][CH2:32]4)[CH:30]=3)[C:16]=2[CH:17]=[N:18][C:19]=1[N+:20]([O-])=O)[CH3:12].Cl>Cl.[Fe].CCO>[NH2:20][C:19]1[N:18]=[CH:17][C:16]2[C:23]([C:26]3[CH:27]=[N:28][N:29]([CH:31]4[CH2:36][CH2:35][N:34]([C:37]([O:39][C:40]([CH3:43])([CH3:41])[CH3:42])=[O:38])[CH2:33][CH2:32]4)[CH:30]=3)=[CH:24][O:25][C:15]=2[C:14]=1[O:13][CH:11]([C:3]1[C:2]([Cl:1])=[C:7]([F:8])[CH:6]=[C:5]([F:9])[C:4]=1[Cl:10])[CH3:12]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 57812426HCID 57812426, compound

Product 1

HCID 57812454HCID 57812454, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

Into a round bottom flask were added tert-Butyl 4-(4-{7-[1-(2,6-dichloro-3,5-difluorophenyl)ethoxy]-6-nitrofuro[3,2-c]pyridin-3-yl}-1H-pyrazol-1-yl)piperidine-1-carboxylate (220 mg, 0.34 mmol), iron (192 mg, 3.44 mmol), 2 drops of 0.1 M HCl and EtOH (7 mL), and the reaction mixture was refluxed for 30 min. 0.1 M HCl was added dropwise and reaction refluxed until consumption of SM was observed. Reaction was stopped and filtered through silica gel washing with 5% MeOH in DCM. Reaction mixture was concentrated in vacuo to obtain the title compound. MS (ES+): m/z 608.06/610.07 (100/70) [MH+]. HPLC: tR=3.74 min (ZQ3, polar—5 min).

Workup

  1. temperaturethe reaction mixture was refluxed for 30 min
  2. customreaction
  3. temperaturerefluxed until consumption of SM
  4. customReaction
  5. filtrationfiltered through silica gel washing with 5% MeOH in DCM
  6. customReaction mixture
  7. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-c60c62b485cd4e9d8c4475af886065f0
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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