Sodium → HCID 178523047, compound

HRID 1949151Notes

Reaction equation

HRID 1949151 reaction equation
[Na].COC(=O)CC[S:7][C:8]1[C:17]([C:18](=[O:26])[NH:19][CH2:20][C:21]2[S:22][CH:23]=[CH:24][CH:25]=2)=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1>CO>[SH:7][C:8]1[C:17]([C:18]([NH:19][CH2:20][C:21]2[S:22][CH:23]=[CH:24][CH:25]=2)=[O:26])=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1

Participants

4

Reactant 2

HCID 5360545SodiumHCID 594862173-[[3-[Oxo-(2-thienylmethylamino)methyl]-2-quinolyl]thio]propanoic acid methyl ester

Product 1

HCID 178523047HCID 178523047, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
70 °C

Procedure

600 mg (26.1 mmol) sodium were added slowly to MeOH (500 ml). Then a solution of 1.16 g (3.0 mmol) 3-[[3-[oxo-(2-thienylmethylamino)methyl]-2-quinolyl]-thio]propanoic acid methyl ester (Example 2) in MeOH (60 ml) was added at RT. Then the reaction solution was heated for 1 h at 70° C. After cooling to RT the mixture was concentrated to small volume under vacuum. The residue was taken up with water and the solution was washed with EE. Then it was acidified with concentrated hydrochloric acid to pH 3. The deposit formed was filtered off and dried. 805 mg (2.7 mmol, 90%) 2-mercapto-N-(thiophen-2-ylmethyl)quinoline-3-carboxamide were obtained.

Workup

  1. temperatureAfter cooling to RT the mixture
  2. concentrationwas concentrated to small volume under vacuum
  3. washthe solution was washed with EE
  4. customThe deposit formed
  5. filtrationwas filtered off
  6. customdried

Sources & evidence

ORD record
ord-49a84d860be34ad88bab140df2c071e9
Source dataset
uspto-grants-2013_03
Patent number
US08399673B2

Reaction notes

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