Hydrochloric Acid → HCID 86591950, compound

HRID 1294069Notes

Reaction equation

HRID 1294069 reaction equation
C([NH:4][C:5]1[CH:25]=[CH:24][C:8]([O:9][C:10]2[N:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][CH:14]([NH:19][C:20](=[O:23])[O:21][CH3:22])[NH:13]3)=[CH:7][CH:6]=1)(=O)C.Cl>O>[NH2:4][C:5]1[CH:25]=[CH:24][C:8]([O:9][C:10]2[N:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][CH:14]([NH:19][C:20](=[O:23])[O:21][CH3:22])[NH:13]3)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86591951HCID 86591951, compound

Product 1

HCID 86591950HCID 86591950, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the MeOH solution, 1,3-bis(methoxycarbonyl)-2-methyl-2-thiopseudourea (1.73 g, 8.4 mmol) was added and stirred at 75° C. After 8 days, AcOH (15 mL) was added and stirred at 80° C. overnight. Additional 1,3-bis(methoxycarbonyl)-2-methyl-2-thiopseudourea (1.73 g, 8.4 mmol) was added then stirred at 80° C. overnight. After cooling, the mixture was poured into NaHCO3 (aq). Formed precipitate was collected by filtration, washed with ethyl acetate then dried under reduced pressure to give methyl (5-(4-acetoamidophenoxy)-3,4-diazaindolin-2-yl)carbamate (983.0 mg, 41%). To a solution of methyl (5-(4-acetoamidophenoxy)-3,4-diazaindolin-2-yl)carbamate (102.4 mg, 0.3 mmol) in water (3 mL) was added 2N HCl (aq) (3.0 mL) then refluxed for 1 hr and stirred at room temperature for 1 hr. The mixture was extracted with ethyl acetate. The organic layer was washed with NH4OH (aq), dried over Na2SO4 then evaporated. Sequence purification on SiO2 column chromatography gave the title compound (33.6 mg, 37%): MS m/e 342 (M+1).

Workup

  1. temperaturethen refluxed for 1 hr
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with NH4OH (aq)
  4. dry with materialdried over Na2SO4
  5. customthen evaporated
  6. customSequence purification on SiO2 column chromatography

Sources & evidence

ORD record
ord-80594dd48e32422bbd32eb1db40be5e8
Source dataset
uspto-grants-2007_07
Patent number
US07238813B2

Reaction notes

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