5-Chloro-1H-indole-2-carboxylic acid → HCID 44450722, compound

HRID 651136Notes

Reaction equation

HRID 651136 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[C:4]([N:6]1[CH2:11][CH2:10][CH:9]([OH:12])[CH2:8][CH2:7]1)=[O:5].[Cl:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[NH:27][C:26]([C:31](O)=[O:32])=[CH:25]2>C(OCC)(=O)C>[OH:20][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][C@H:3]([NH:2][C:31]([C:26]2[NH:27][C:28]3[C:24]([CH:25]=2)=[CH:23][C:22]([Cl:21])=[CH:30][CH:29]=3)=[O:32])[C:4]([N:6]2[CH2:7][CH2:8][CH:9]([OH:12])[CH2:10][CH2:11]2)=[O:5])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 69688232HCID 69688232, compound

Product 1

HCID 44450722HCID 44450722, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(S)-2-Amino-3-(4-hydroxy-phenyl)-1-(4-hydroxy-piperidin-1-yl)-propan-1-one hydrochloride (0.68 mmol) and 5-chloro-1H-indole-2-carboxylic acid (0.65 mmol) were coupled according to Procedure A (0-25° C. reaction temperature) with the following workup: the reaction mixture was diluted with ethyl acetate, the resulting solution washed with 1N NaOH (2 ml), the aqueous layer extracted three times with ethyl acetate, the combined organic extracts washed with 1N HCl, dried and concentrated. The residue was purified by chromatography on silica gel eluted with 1-16% ethanol in dichloromethane. Yield, 150 mg, 52%; HPLC (60/40) 3.53 minutes (99%); PBMS 442/444 (MH+, 100%);

Workup

  1. washthe resulting solution washed with 1N NaOH (2 ml)
  2. extractionthe aqueous layer extracted three times with ethyl acetate
  3. washthe combined organic extracts washed with 1N HCl
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel
  7. washeluted with 1-16% ethanol in dichloromethane
  8. customYield

Sources & evidence

ORD record
ord-93aa3709e515405e804383095be976e6
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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