Sodium Carbonate → HCID 86699719, compound

HRID 1844108Notes

Reaction equation

HRID 1844108 reaction equation
ClC(OC(=O)OC(Cl)(Cl)Cl)(Cl)Cl.[CH3:13][N:14]1[CH2:18][CH2:17][N:16]([C:19](Cl)=[O:20])[C:15]1=[O:22].[NH2:23][C:24]1[CH:32]=[C:31]2[C:27]([CH2:28][C:29](=[O:33])[NH:30]2)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1>[CH3:13][N:14]1[CH2:18][CH2:17][N:16]([C:19]([NH:23][C:24]2[CH:32]=[C:31]3[C:27]([CH2:28][C:29](=[O:33])[NH:30]3)=[CH:26][CH:25]=2)=[O:20])[C:15]1=[O:22]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 94429TriphosgeneHCID 5905386-Amino-1,3-dihydro-2H-indol-2-oneHCID 205593403-Methyl-2-oxoimidazolidine-1-carbonyl chloride

Product 1

HCID 86699719HCID 86699719, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

bis(trichloromethyl)carbonate in tetrahydrofuran was added dropwise within 1 hour to the compound D78 in tetrahydrofuran in such a way that the internal temperature was kept at 55-60° C. The mixture was stirred for 5 h at this temperature. The formation of 3-methyl-2-oxoimidazolidine-1-carbonyl chloride was confirmed by TLC. The 6-aminoindolin-2-one (D4) was added to the mixture in situ and the mixture was refluxed for 4 h. The completion of reaction was monitored using TLC. The residue obtained after workup using saturated sodium carbonate was further purified using flash chromatography on silica gel to afford the title compound D79.

Workup

  1. customwas kept at 55-60° C
  2. temperaturethe mixture was refluxed for 4 h
  3. customThe completion of reaction
  4. customThe residue obtained after workup
  5. customwas further purified

Sources & evidence

ORD record
ord-317dbfc389ca4de084b3ea04c288ea6c
Source dataset
uspto-grants-2015_02
Patent number
US08946282B2

Reaction notes

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