5-Chloro-1H-indole-2-carboxylic acid → HCID 44450821, compound

HRID 1872154Notes

Reaction equation

HRID 1872154 reaction equation
Cl.Cl.[NH2:3][C@@H:4]([CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[C:5]([N:7]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]1)=[O:6].[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>>[OH:13][CH:10]1[CH2:11][CH2:12][N:7]([C:5](=[O:6])[C@@H:4]([NH:3][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])[CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH2:8][CH2:9]1

Participants

3

Reactant 2

HCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 69687368HCID 69687368, compound

Product 1

HCID 44450821HCID 44450821, compound

Procedure

(S)-2-Amino-1-(4-hydroxy-piperidin-1-yl)-3-pyridin-3-yl-propan-1-one dihydrochloride (0.8 mmol) and 5-chloro-1H-indole-2-carboxylic acid (0.7 mmol) were coupled according to Procedure A (0-25° C. reaction temperature) and the product purified by chromatography on silica gel eluted with 1-16% ethanol in dichloromethane. Yield 26 mg, 8%; HPLC (50/50) 5.02 minutes (99%); PBMS 427/429 (MH+, 100%);

Workup

  1. customthe product purified by chromatography on silica gel
  2. washeluted with 1-16% ethanol in dichloromethane
  3. customHPLC (50/50) 5.02 minutes (99%)

Sources & evidence

ORD record
ord-deb82d514180425aa0dd5749955d99e6
Source dataset
uspto-grants-2000_08
Patent number
US06107329

Reaction notes

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