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Phosgene → N-(3,5-dimethyl-4-{(E)-2-[4-oxo-2-(3-trifluoromethoxy-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-vinyl}-phenyl)-N-methyl-chloroformamide

HRID 1755050
Notes
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Reaction equation

HRID 1755050 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].[CH3:5][C:6]1[CH:11]=[C:10]([NH:12][CH3:13])[CH:9]=[C:8]([CH3:14])[C:7]=1/[CH:15]=[CH:16]/[S:17]([N:20]1[CH2:41][CH2:40][C:23]2([N:27]=[C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([O:34][C:35]([F:38])([F:37])[F:36])[CH:29]=3)[NH:25][C:24]2=[O:39])[CH2:22][CH2:21]1)(=[O:19])=[O:18].C(N(CC)CC)C>ClCCl.CN(C)C=O>[CH3:5][C:6]1[CH:11]=[C:10]([N:12]([CH3:13])[C:1]([Cl:4])=[O:2])[CH:9]=[C:8]([CH3:14])[C:7]=1/[CH:15]=[CH:16]/[S:17]([N:20]1[CH2:21][CH2:22][C:23]2([N:27]=[C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([O:34][C:35]([F:36])([F:38])[F:37])[CH:29]=3)[NH:25][C:24]2=[O:39])[CH2:40][CH2:41]1)(=[O:18])=[O:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 66816601HCID 66816601, compound

Product 1

HCID 86672781N-(3,5-dimethyl-4-{(E)-2-[4-oxo-2-(3-trifluoromethoxy-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-vinyl}-phenyl)-N-methyl-chloroformamideYield 85%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 6344DichloromethaneSolvent

Procedure

Phosgene (20% solution in toluene, 35 μL, 67 μmol) was added to a mixed solution of 8-[(E)-2-(2,6-dimethyl-4-methylamino-phenyl)-ethenesulfonyl]-2-(3-trifluoromethoxy-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (30 mg, 56 μmol) and triethylamine (15 μL, 84 μmol) in dichloromethane (1.5 ml) and dimethylformamide (0.5 ml) at 0° C. The mixture was stirred at room temperature for three hours, and then quenched with water and extracted with ethyl acetate. The organic layer was sequentially washed with water and saturated brine, and then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (dichloromethane-ethyl acetate) to give N-(3,5-dimethyl-4-{(E)-2-[4-oxo-2-(3-trifluoromethoxy-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-vinyl}-phenyl)-N-methyl-chloroformamide (28 mg, 85%).

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was sequentially washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (dichloromethane-ethyl acetate)

Sources & evidence

ORD record
ord-6eccd0a5883949b9bd4f472c4de9ba87
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09169254B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes