Dimethylacetamide → HCID 66816400, compound

HRID 1754955Notes

Reaction equation

HRID 1754955 reaction equation
ClC(OC1C=CC([N+]([O-])=O)=CC=1)=O.[CH3:14][C:15]1[CH:20]=C(NC)[CH:18]=[CH:17][C:16]=1/[CH:23]=[CH:24]/[S:25]([N:28]1[CH2:49][CH2:48][C:31]2([N:35]=[C:34]([C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([O:42][C:43]([F:46])([F:45])[F:44])[CH:37]=3)[NH:33][C:32]2=[O:47])[CH2:30][CH2:29]1)(=[O:27])=[O:26].[CH3:50][N:51]([CH3:55])[CH2:52][CH2:53][NH2:54].C[C:57]([N:59]([CH3:61])[CH3:60])=[O:58]>C1COCC1>[CH3:50][N:51]([CH3:55])[CH2:52][CH2:53][NH:54][C:57](=[O:58])[N:59]([CH3:61])[C:60]1[CH:18]=[CH:17][C:16](/[CH:23]=[CH:24]/[S:25]([N:28]2[CH2:29][CH2:30][C:31]3([N:35]=[C:34]([C:36]4[CH:41]=[CH:40][CH:39]=[C:38]([O:42][C:43]([F:45])([F:44])[F:46])[CH:37]=4)[NH:33][C:32]3=[O:47])[CH2:48][CH2:49]2)(=[O:26])=[O:27])=[C:15]([CH3:20])[CH:14]=1

Participants

6

Reactant 4

HCID 31374DimethylacetamideHCID 66053N,N-DimethylethylenediamineHCID 821294-Nitrophenyl chloroformateHCID 66816396HCID 66816396, compound

Product 1

HCID 66816400HCID 66816400, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

4-Nitrophenyl chloroformate (35 mg, 0.17 mmol) was added to a solution of 8-[(E)-2-(2-methyl-4-methylamino-phenyl)-ethenesulfonyl]-2-(3-trifluoromethoxy-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (80 mg, 0.15 mmol) in THF (1 ml) at room temperature, and the mixture was then stirred at 70° C. for 30 minutes. The reaction mixture was extracted with AcOEt, and then dried over sodium sulfate and concentrated under reduced pressure. The resulting intermediate (83a) (20 mg, 0.029 mmol) was dissolved in DMA (0.1 ml), and N,N-dimethylethylenediamine (0.1 ml, 0.91 mmol) was added. The mixture was then stirred at 140° C. for one hour and at 100° C. for one hour. The resulting reaction mixture was purified by silica gel column chromatography to give 3-(2-dimethylamino-ethyl)-1-methyl-1-(3-methyl-4-{(E)-2-[4-oxo-2-(3-trifluoromethoxy-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-vinyl}-phenyl)-urea as an amorphous (12 mg, yield 66%).

Workup

  1. extractionThe reaction mixture was extracted with AcOEt
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. stirringThe mixture was then stirred at 140° C. for one hour and at 100° C. for one hour
  5. customThe resulting reaction mixture
  6. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-74646c3ecfe54587a244d83f8230ed81
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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