Acetone → HCID 59424924, compound

HRID 907157Notes

Reaction equation

HRID 907157 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) was treated with HCl (3 mL, 6 N), and the resulting solution was heated to reflux overnight. The reaction mixture was cooled, and the resulting precipitate was 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 was heated
  2. temperatureto reflux overnight
  3. temperatureThe reaction mixture was cooled
  4. filtrationthe resulting precipitate was collected by filtration
  5. washwashed with ether
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-1f3433fec0b24318861c715c9f5e1bc5
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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