5-Chloro-1H-indole-2-carboxylic acid → HCID 10574415, compound

HRID 651123Notes

Reaction equation

HRID 651123 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[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:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[NH:26][C:25]([C:30](O)=[O:31])=[CH:24]2>>[CH2:13]([C@H:3]([NH:2][C:30]([C:25]1[NH:26][C:27]2[C:23]([CH:24]=1)=[CH:22][C:21]([Cl:20])=[CH:29][CH:28]=2)=[O:31])[C:4]([N:6]1[CH2:11][CH2:10][CH:9]([OH:12])[CH2:8][CH2:7]1)=[O:5])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 69688479HCID 69688479, compound

Product 1

HCID 10574415HCID 10574415, compound

Procedure

(S)-2-Amino-1-(4-hydroxy-piperidin-1-yl)-3-phenyl-propan-1-one hydrochloride (0.8 mmol) and 5-chloro-1H-indole-2-carboxylic acid (0.9 mmol) were coupled according to Procedure A (0-25° C. reaction temperature, 48 hour reaction time) and the product purified by chromatography on silica gel eluted with 50, 75 and 100% ethyl acetate in hexanes followed by trituration from 1:1 ether-hexanes. Yield 266 mg, 76%; HPLC (60/40) 4.09 minutes (99%); PBMS 426/428 (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) 4.09 minutes (99%)

Sources & evidence

ORD record
ord-4e5ac52c0f944652be062791c0b34b2e
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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