5-Chloro-1H-indole-2-carboxylic acid → HCID 9843776, compound

HRID 1872209Notes

Reaction equation

HRID 1872209 reaction equation
Cl.[NH2:2][CH:3]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:4]([N:6]1[CH2:9][CH:8]([OH:10])[CH2:7]1)=[O:5].[Cl:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][C:23]([C:28](O)=[O:29])=[CH:22]2>ClCCl.CN(C)C=O>[CH2:11]([C@H:3]([NH:2][C:28]([C:23]1[NH:24][C:25]2[C:21]([CH:22]=1)=[CH:20][C:19]([Cl:18])=[CH:27][CH:26]=2)=[O:29])[C:4]([N:6]1[CH2:7][CH:8]([OH:10])[CH2:9]1)=[O:5])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 22610288HCID 22610288, compound

Product 1

HCID 9843776HCID 9843776, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

2-Amino-1-(3-hydroxy-azetidin-1-yl)-3-phenyl-propan-1-one hydrochloride (1.18 mmol) and 5-chloro-1H-indole-2-carboxylic acid (1.1 8 mmol) were coupled according to Procedure A (4:1 dichloromethane-dimethylformamide reaction solvent) and the product purified by chromatography on silica gel eluted with 25%, 50%, 75% and 100% ethyl acetate-hexanes giving the title substance as a colorless foam (104 mg, 22%). A mixture (180 mg) of less polar products was also isolated. Title substance: HPLC (60/40) 4.18 minutes (97%); TSPMS 398/400 (MH+, 100%);

Workup

  1. customthe product purified by chromatography on silica gel
  2. washeluted with 25%, 50%, 75% and 100% ethyl acetate-hexanes giving the title substance as a colorless foam (104 mg, 22%)

Sources & evidence

ORD record
ord-53b6c4660d2245e0a3bf71203cf93203
Source dataset
uspto-grants-2000_08
Patent number
US06107329

Reaction notes

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