Water → HCID 57975048, compound

HRID 1865076Notes

Reaction equation

HRID 1865076 reaction equation
C1CCN2C(=NCCC2)CC1.[CH2:12]([O:14][C:15]([C:17]1[N:18]([CH3:40])[C:19]([CH2:38][CH3:39])=[C:20]([C:36]#[N:37])[C:21]=1[C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[NH2:35])=[CH:24][CH:23]=1)=[O:16])[CH3:13].[CH:41]([S:44](Cl)(=[O:46])=[O:45])([CH3:43])[CH3:42].O>C(Cl)Cl>[CH2:12]([O:14][C:15]([C:17]1[N:18]([CH3:40])[C:19]([CH2:38][CH3:39])=[C:20]([C:36]#[N:37])[C:21]=1[C:22]1[CH:23]=[CH:24][C:25]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[NH:35][S:44]([CH:41]([CH3:43])[CH3:42])(=[O:46])=[O:45])=[CH:26][CH:27]=1)=[O:16])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 824082-Propanesulfonyl chlorideHCID 57974946HCID 57974946, compound

Product 1

HCID 57975048HCID 57975048, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Add DBU (0.29 mL, 1.92 mmol) to 3-[4-(2-amino-phenoxy)-phenyl]-4-cyano-5-ethyl-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (0.25 g, 0.64 mmol, prepared in example E-95) in methylene chloride at room temperature with stirring. After 10 minutes, cool to 0° C. and add isopropyl-sulfonylchloride (0.11 mL, 0.96 mmol). Stir the reaction mixture at 0° C. for 30 minutes and then at room temperature for 2-6 hours. Then pour the reaction mixture into water and extract with methylene chloride. Combine the organic extracts, wash with 1N HCl, water and brine, dry over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure. Purify the residue by flash chromatography eluting with acetonitrile:methylene chloride to provide the title compound.

Workup

  1. stirringStir the reaction mixture at 0° C. for 30 minutes
  2. waitat room temperature for 2-6 hours
  3. extractionextract with methylene chloride
  4. washwash with 1N HCl, water and brine
  5. dry with materialdry over anhydrous magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under reduced pressure
  8. customPurify the residue by flash chromatography
  9. washeluting with acetonitrile

Sources & evidence

ORD record
ord-02d738726e5041bdb33095cd22d1c593
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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