HCID 57771773, compound → HCID 57771696, compound

HRID 1174954Notes

Reaction equation

HRID 1174954 reaction equation
[CH3:1][N:2]([CH:15]1[CH2:20][CH2:19][CH2:18][N:17]([CH3:21])[CH2:16]1)[C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][C:6]=2[N:7]=1>C(O)(=O)C.[Fe]>[NH3:2].[CH3:1][N:2]([CH:15]1[CH2:20][CH2:19][CH2:18][N:17]([CH3:21])[CH2:16]1)[C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 1

HCID 57771773HCID 57771773, compound

Product 2

HCID 222AmmoniaYield 10%HCID 57771696HCID 57771696, compoundYield 195.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

Place methyl-(1-methyl-piperidin-3-yl)-(5-nitro-benzooxazol-2-yl)-amine (440 mg, 1.51 mmol) and iron powder (423 mg, 7.58 mmol) in acetic acid (10 mL). Heat the reaction to 40° C. for 2 h. Cool to rt and then load onto a Varian™ SCX column. Wash the column with methanol and DCM. Flush the compound off the column by eluting with 2M NH3 in methanol. Collect filtrate and concentrate in vacuo. Chromatograph (silica gel, eluting with 0-10% 2M NH3 in MeOH:DCM, then 10% 2M NH3 in MeOH:DCM) to yield 385 mg (98%) of the title compound: mass spectrum (ion-spray): (m/z)=261.3 (M+1).

Workup

  1. temperatureHeat
  2. customthe reaction to 40° C. for 2 h
  3. washWash the column with methanol and DCM
  4. customFlush the compound off the column
  5. washby eluting with 2M NH3 in methanol
  6. concentrationCollect filtrate and concentrate in vacuo
  7. washChromatograph (silica gel, eluting with 0-10% 2M NH3 in MeOH

Sources & evidence

ORD record
ord-edc41679ed2346ec92d5590652fdfe01
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

Loading…