Hydrochloric Acid → HCID 9797312, compound

HRID 651121Notes

Reaction equation

HRID 651121 reaction equation
Cl.[NH2:2][CH2:3][C:4]([N:6]1[CH2:10][CH2:9][S:8][CH2:7]1)=[O:5].[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16]([C:21](O)=[O:22])=[CH:15]2.Cl>C(OCC)(=O)C>[O:5]=[C:4]([N:6]1[CH2:10][CH2:9][S:8][CH2:7]1)[CH2:3][NH:2][C:21]([C:16]1[NH:17][C:18]2[C:14]([CH:15]=1)=[CH:13][C:12]([Cl:11])=[CH:20][CH:19]=2)=[O:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 21710733HCID 21710733, compound

Product 1

HCID 9797312HCID 9797312, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Amino-1-thiazolidin-3-yl-ethanone hydrochloride (3.1 mmol) and 5-chloro-1H-indole-2-carboxylic acid (3.4 mmol) were coupled according to Procedure A (0-25° C., 120 hour reaction time) substituting the following work up: the reaction mixture was stirred with ethyl acetate and 2N HCl, filtered, and the filtered solid washed with 2N HCl, 2N NaOH and ether. Yield 988 mg, 98%; HPLC (70/30) 3.25 minutes (99%); mp 253-255° C. (dec, darkening at 243° C.); PBMS 324/326 (MH+, 100%);

Workup

  1. filtrationfiltered
  2. washthe filtered solid washed with 2N HCl, 2N NaOH and ether
  3. customHPLC (70/30) 3.25 minutes (99%)
  4. custommp 253-255° C. (dec, darkening at 243° C.)

Sources & evidence

ORD record
ord-2bba44e726434c9e8be8e01fca471f72
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

Loading…