5-Chloro-1H-indole-2-carboxylic acid → HCID 44450822, compound

HRID 1872147Notes

Reaction equation

HRID 1872147 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl: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>>[Cl: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

3

Reactant 2

HCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 69688622HCID 69688622, compound

Product 1

HCID 44450822HCID 44450822, compound

Procedure

(S)-2-Amino-3-(4-chloro-phenyl)-1-(4-hydroxy-piperidin-1-yl)-propan-1-one hydrochloride (0.98 mmol) and 5-chloro-1H-indole-2-carboxylic acid (0.92 mmol) were coupled according to Procedure A and the product purified by chromatography on silica gel eluted with 50, 75 and 100% ethyl acetate in hexanes. Yield 362 mg, 86%; HPLC (60/40) 5.06 minutes (97%); mp 227-229° C.; TSPMS 460/462 (MH+, 100%);

Workup

  1. customthe product purified by chromatography on silica gel
  2. washeluted with 50, 75 and 100% ethyl acetate in hexanes
  3. customHPLC (60/40) 5.06 minutes (97%)

Sources & evidence

ORD record
ord-e394ca665fa144cfb32140b631176839
Source dataset
uspto-grants-2000_08
Patent number
US06107329

Reaction notes

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