Dimethylformamide → HCID 66585051, compound

HRID 1630032Notes

Reaction equation

HRID 1630032 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:10]3[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13][CH2:12][N:11]3[CH:23]=2)[CH:5]=[CH:6][CH:7]=1.ClS([N:33]=[C:34]=O)(=O)=O.CN(C)C=O.[OH-].[Na+]>ClCCl>[C:34]([C:23]1[N:11]2[CH2:12][CH2:13][N:14]([C:16]([O:18][C:19]([CH3:21])([CH3:22])[CH3:20])=[O:17])[CH2:15][C:10]2=[C:9]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:8]=1[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1)#[N:33]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 70918Chlorosulfonyl isocyanateHCID 66584850HCID 66584850, compound

Product 1

HCID 66585051HCID 66585051, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution, under argon and cooled to 10° C., of 2.52 g (6.49 mmol) of 2-tert-butyl 8-ethyl 7-(3-fluorophenyl)-3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1H)-dicarboxylate in 20 ml of dichloromethane is added dropwise 0.62 ml (7.14 mmol) of chlorosulfonyl isocyanate (CAS 1189-71-5) and the mixture is left stirring at 0° C. for 1 hour. 3.3 ml (65 mmol) of dimethylformamide are then added dropwise to the mixture, cooled to −10° C. After stirring for 5 hours at room temperature, the mixture is poured into 60 ml of aqueous 1N sodium hydroxide solution and the product is extracted with dichloromethane. The solution is dried over sodium sulfate and the solvent is evaporated off under reduced pressure, to give a yellow oil, which is chromatographed on a column of g of silica gel, eluting with a mixture of 20% ethyl acetate in cyclohexane, to give 1.24 g of 2-tert-butyl 8-ethyl 6-cyano-7-(3-fluorophenyl)-3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1H)-dicarboxylate in the form of a white powder after crystallizing from diisopropyl ether, filtering off and drying.

Workup

  1. waitthe mixture is left
  2. temperaturecooled to −10° C
  3. stirringAfter stirring for 5 hours at room temperature
  4. extractionthe product is extracted with dichloromethane
  5. dry with materialThe solution is dried over sodium sulfate
  6. customthe solvent is evaporated off under reduced pressure
  7. customto give a yellow oil, which
  8. customis chromatographed on a column of g of silica gel
  9. washeluting with a mixture of 20% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-efab12f0ae4e448ebf4e4624e88a8a62
Source dataset
uspto-grants-2014_07
Patent number
US08791119B2

Reaction notes

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