Acetone → HCID 59424924, compound

HRID 502175Notes

Reaction equation

HRID 502175 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:13][CH3:14])=[CH:9][CH:10]=2)[N:5]([CH2:15][CH3:16])[C:4]=1[C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:32])[NH:25][CH2:26][C:27](OCC)=[O:28])=[CH:19][CH:18]=1)#[N:2].Cl.CC(C)=[O:36]>>[CH2:13]([O:12][C:8]1[CH:7]=[C:6]2[C:11]([C:3]([C:1]([NH2:2])=[O:36])=[C:4]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[C:27](=[O:28])[CH2:26][NH:25][C:24]4=[O:32])=[CH:19][CH:18]=3)[N:5]2[CH2:15][CH3:16])=[CH:10][CH:9]=1)[CH3:14]

Participants

4

Reactant 3

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 59424910HCID 59424910, compound2×

Product 1

HCID 59424924HCID 59424924, compoundYield 87%

Procedure

A solution of ethyl {3-[4-(3-cyano-6-ethoxy-1-ethyl-1H-indol-2-yl)-phenyl]-ureido}acetate (compound 773, 325 mg, 0.748 mmol), prepared in procedure 1AV, step A, in acetone (5 mL) is treated with HCl (3 mL, 6 N), and the resulting solution is heated to reflux overnight. The reaction mixture is cooled, and the resulting precipitate is collected by filtration, washed with ether and dried under high vacuum to afford the product, 6-ethoxy-1-ethyl-2-[4-(2,5-dioxo-imidazolidin-1-yl)-phenyl]-1H-indole-3-carboxamide (264 mg, 0.650 mmol, 87%).

Workup

  1. temperaturethe resulting solution is heated
  2. temperatureto reflux overnight
  3. temperatureThe reaction mixture is cooled
  4. filtrationthe resulting precipitate is collected by filtration
  5. washwashed with ether
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-6979e277f3984af6a81e7d824daa4da5
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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