Ammonia → HCID 178500075, compound

HRID 1452900Notes

Reaction equation

HRID 1452900 reaction equation
I[Si](C)(C)C.[CH3:6][S:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:16]([NH:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[N:25](C(OC(C)(C)C)=O)[N:24]=[C:23]2/[CH:36]=[CH:37]/[C:38]([O:40][CH3:41])=[O:39])(=[O:18])=[O:17])(=[O:9])=[O:8].N>C(Cl)(Cl)Cl>[CH3:6][S:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:16]([NH:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][N:24]=[C:23]2/[CH:36]=[CH:37]/[C:38]([O:40][CH3:41])=[O:39])(=[O:17])=[O:18])(=[O:9])=[O:8]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 85247Trimethylsilyl iodideHCID 68874812HCID 68874812, compound

Product 1

HCID 178500075HCID 178500075, compoundYield 15.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
20 °C

Procedure

Methyl(E)-3-[5(2-methylsulfonylbenzenesulfonylamino)-1H-indazol-3-yl]-acrylate can be obtained in the following way: 40 μl of iodotrimethylsilane are added dropwise to a solution, maintained under an atmosphere of argon, of 150 mg of methyl(E)-3-[5(2-methylsulfonylbenzenesulfonylamino)-1-tert-butoxycarbonylindazol-3-yl]acrylate in 10 ml of chloroform, and the mixture is stirred at a temperature in the region of 20° C. for 16 hours. 5 ml of an aqueous solution containing 5% of aqueous ammonia are then added and the medium is extracted with dichloromethane. The pooled organic extracts are washed with distilled water, dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure. The white foam thus isolated is recrystallized from 8 ml of acetonitrile. 19 mg of methyl(E)-3-[5(2-methylsulfonylbenzenesulfonylamino)-1H-indazol-3-yl]-acrylate are thus obtained in the form of a white solid melting at 253° C. (analysis C18H17N3O6S2 % calculated C, 49.65; H, 3.93; N, 9.65; O, 22.04; S, 14.73. % found C, 49.14; H, 3.92; N, 9.47; S, 14.23).

Workup

  1. additionare then added
  2. extractionthe medium is extracted with dichloromethane
  3. washThe pooled organic extracts are washed with distilled water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customThe white foam thus isolated
  8. customis recrystallized from 8 ml of acetonitrile

Sources & evidence

ORD record
ord-b396ec2600c541e19db886c50d50df68
Source dataset
uspto-grants-2009_01
Patent number
US07473701B2

Reaction notes

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