Dimethylformamide → HCID 59576368, compound

HRID 2069517Notes

Reaction equation

HRID 2069517 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[F:25])[CH2:5][N:6]1[CH:10]=[C:9]([S:11]([C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)(=[O:13])=[O:12])[CH:8]=[C:7]1[C:19]([OH:21])=O.CN(C)C=O.S(Cl)(Cl)=O.Cl.[Cl:36][C:37]1[S:41][C:40]([NH2:42])=[N:39][CH:38]=1>ClC(Cl)C.ClCCl.O.N1C=CC=CC=1>[Cl:36][C:37]1[S:41][C:40]([NH:42][C:19]([C:7]2[N:6]([CH2:5][C:4]3[CH:22]=[CH:23][C:24]([F:25])=[C:2]([F:1])[CH:3]=3)[CH:10]=[C:9]([S:11]([C:14]3[S:15][CH:16]=[CH:17][CH:18]=3)(=[O:13])=[O:12])[CH:8]=2)=[O:21])=[N:39][CH:38]=1

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 1487432-Amino-5-chlorothiazole hydrochlorideHCID 59576357HCID 59576357, compound

Product 1

HCID 59576368HCID 59576368, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-(3,4-difluoro-benzyl)-4-(thiophene-2-sulfonyl)-1H-pyrrole-2-carboxylic acid (D1-3) in dichloroethane was added catalytic amount of dimethylformamide and thionyl chloride at 0-5° C. Reaction mixture was heated at 80° C. for 6 hrs and concentrated in inert atmosphere, resulting residue was dissolved in dichloromethane and was added drop wise to mixture of pyridine (1 ml) and 5-chloro-thiazol-2-ylamine hydrochloride at 0° C. The reaction was maintained at 40-50° C. overnight. Water was added to reaction mixture and extracted with dichloromethane. The organic layer was washed with water and brine, dried over anhydrous sodium sulphate, filtered and concentrated to afford 1-(3,4-difluoro-benzyl)-4-(thiophene-2-sulfonyl)-1H-pyrrole-2-carboxylic acid (5-chloro-thiazol-2-yl)-amide (D1).

Workup

  1. customReaction mixture
  2. concentrationconcentrated in inert atmosphere
  3. customresulting residue
  4. additionwas added drop
  5. temperatureThe reaction was maintained at 40-50° C. overnight
  6. extractionextracted with dichloromethane
  7. washThe organic layer was washed with water and brine
  8. dry with materialdried over anhydrous sodium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-9bc55f3f4640493099e660bfcbd27d86
Source dataset
uspto-grants-2012_10
Patent number
US08299115B2

Reaction notes

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