5-cyano-1H-indole-2-carboxylic Acid → 5-Cyano-1H-indole-2-carboxylic acid ((1S)-benzyl-2-oxo-2-thiazolidin-3-yl-ethyl)-amide

HRID 651119Notes

Reaction equation

HRID 651119 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:4]([N:6]1[CH2:10][CH2:9][S:8][CH2:7]1)=[O:5].[C:18]([C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:24]([C:29](O)=[O:30])=[CH:23]2)#[N:19]>C(OCC)(=O)C.Cl>[CH2:11]([C@H:3]([NH:2][C:29]([C:24]1[NH:25][C:26]2[C:22]([CH:23]=1)=[CH:21][C:20]([C:18]#[N:19])=[CH:28][CH:27]=2)=[O:30])[C:4](=[O:5])[N:6]1[CH2:10][CH2:9][S:8][CH2:7]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 71446255-cyano-1H-indole-2-carboxylic AcidHCID 69687431(S)-2-Amino-3-phenyl-1-thiazolidin-3-yl-propan-1-one hydrochloride

Product 1

HCID 570888895-Cyano-1H-indole-2-carboxylic acid ((1S)-benzyl-2-oxo-2-thiazolidin-3-yl-ethyl)-amide

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

(S)-2-Amino-3-phenyl-1-thiazolidin-3-yl-propan-1-one hydrochloride (4.0 mmol) and 5-cyano-1H-indole-2-carboxylic acid (4.0 mmol) were coupled according to Procedure A (0-25° C. reaction temperature, 48 hours reaction time) with the following workup: the reaction mixture was diluted with ethyl acetate and 2 N HCl, the resulting precipitate collected by filtration, washed with 2 N HCl and 2 N NaOH. The crude product was purified by chromatography on silica gel eluted with 30, 40 and 60% ethyl acetate in hexanes. Yield 1.22 g, 75%; HPLC (60/40) 4.74 minutes (97%); PBMS 405 (MH+, 100%);

Workup

  1. filtrationthe resulting precipitate collected by filtration
  2. washwashed with 2 N HCl and 2 N NaOH
  3. customThe crude product was purified by chromatography on silica gel
  4. washeluted with 30, 40 and 60% ethyl acetate in hexanes
  5. customHPLC (60/40) 4.74 minutes (97%)

Sources & evidence

ORD record
ord-6fda81657fd44e429e1c7fb2788f9671
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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