Dimethylformamide → HCID 19837972, compound

HRID 2291579Notes

Reaction equation

HRID 2291579 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[N:10]([CH2:11][C:12]([OH:14])=O)[C:9](=[O:15])[S:8][C:5]2=[N:6][CH:7]=1.O[N:17]1[C:21](=O)[CH2:20][CH2:19][C:18]1=O.C[N:25](C)C=O>>[Cl:1][C:2]1[CH:3]=[C:4]2[N:10]([CH2:11][C:12]([N:17]3[CH2:21][CH2:20][NH:25][CH2:19][CH2:18]3)=[O:14])[C:9](=[O:15])[S:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 80170N-HydroxysuccinimideHCID 11010206HCID 11010206, compound

Product 1

HCID 19837972HCID 19837972, compound

Procedure

To an ice-cooled solution of a mixture of 6-chloro-1-carboxymethyl-2-oxo-1,2-dihydrothiazolo[5,4-b]pyridine (3.47 g) and N-hydroxysuccinimide (1.96 g) in N,N-dimethylformamide (20 ml) was gradually added N,N-dicyclohexylcarbodiimide (3.51 g). The mixture was stirred for 1 hour at ambient temperature and dicyclohexylurea that precipitated from the reaction mixture was removed by filtration. To a solution of piperazine (6.11 g) in N,N-dimethylformamide (80 ml) was added dropwise the filtrate for a period of 1.5 hours below 20° c. The final mixture was stirred for 4 hours at ambient temperature, and then filtered. The filtrate was concentrated under reduced pressure below 50° C. and the residue was dissolved in 2N hydrochloric acid. The aqueous solution was washed with chloroform and then adjusted to pH 9 with an aqueous solution of sodium hydrogen carbonate. The turbid solution was extracted with chloroform, and the extract was dried over magnesium sulfate and concentrated under reduced pressure to give a white powder of 6-choro-2-oxo-1-[(1-piperazinyl)carbonylmethyl]-1,2-dihydrothiazolo[5,4 -b]pyridine (3.24 g).

Workup

  1. customdicyclohexylurea that precipitated from the reaction mixture
  2. customwas removed by filtration
  3. additionTo a solution of piperazine (6.11 g) in N,N-dimethylformamide (80 ml) was added dropwise the filtrate for a period of 1.5 hours below 20° c
  4. stirringThe final mixture was stirred for 4 hours at ambient temperature
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure below 50° C.
  7. dissolutionthe residue was dissolved in 2N hydrochloric acid
  8. washThe aqueous solution was washed with chloroform
  9. extractionThe turbid solution was extracted with chloroform
  10. dry with materialthe extract was dried over magnesium sulfate
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-091ec2f0ad2445b4ba6b64880afa5eb4
Source dataset
uspto-grants-1989_01
Patent number
US04797399

Reaction notes

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