Hydrochloric Acid → HCID 22012009, compound

HRID 1533001Notes

Reaction equation

HRID 1533001 reaction equation
[SH:1]CCC(OC)=O.[H-].[Na+].[Cl:10][C:11]1[C:12]([C:27]([NH2:29])=[O:28])=[C:13]2[N:18]([C:19]=1[C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)[CH2:17][CH2:16][C:15](Cl)=[CH:14]2.Cl>CN(C)C=O.O>[Cl:10][C:11]1[C:12]([C:27]([NH2:29])=[O:28])=[C:13]2[N:18]([C:19]=1[C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)[CH2:17][CH2:16][C:15]([SH:1])=[CH:14]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 18050Methyl 3-mercaptopropionateHCID 24758Sodium hydrideHCID 15406815HCID 15406815, compound

Product 1

HCID 22012009HCID 22012009, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
68 °C

Procedure

2.4 g of methyl 3-mercaptopropionate are dissolved in 100 cm3 of dimethylformamide. 0.8 g of sodium hydride is added in small fractions, and then 3.08 g of 2,7-dichloro-3-pyridin-3-yl-5,6-dihydroindolizine-1-carboxamide in 80 cm3 of dimethylformamide are poured in. The mixture is heated at 68° C. for 2 hours 30 minutes, and then poured into 25 cm3 of hydrochloric acid (4 N). The mixture is concentrated to dryness under reduced pressure (1 kPa) at a temperature close to 60° C. The yellow residue obtained is taken up in 280 cm3 of water and 10 cm3 of hydrochloric acid (2 N), and then filtered and washed with twice 5 cm3 of water. 1.1 g of 2-chloro-3-pyridin-3-yl-7-mercapto-5,6-dihydroindolizine-1-carboxamide are thus obtained in the form of a yellow powder melting at 232° C.

Workup

  1. concentrationThe mixture is concentrated to dryness under reduced pressure (1 kPa) at a temperature
  2. customclose to 60° C
  3. customThe yellow residue obtained
  4. filtration10 cm3 of hydrochloric acid (2 N), and then filtered
  5. washwashed with twice 5 cm3 of water

Sources & evidence

ORD record
ord-1ec2f5763a83456db0bf7c8781021d1b
Source dataset
uspto-grants-2001_03
Patent number
US06207675B1

Reaction notes

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