5-Fluoroindole-2-carboxylic acid → HCID 44450787, compound

HRID 651114Notes

Reaction equation

HRID 651114 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].[F: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]([F: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 18205-Fluoroindole-2-carboxylic acidHCID 69688479HCID 69688479, compound

Product 1

HCID 44450787HCID 44450787, compound

Procedure

(S)-2-Amino-1-(4-hydroxy-piperidin-1-yl)-3-phenyl-propan-1-one hydrochloride (0.65 mmol) and 5-fluoro-1H-indole-2-carboxylic acid (0.73 mmol) were coupled according to Procedure A (0-25° C. reaction temperature) and the product purified by chromatography on silica gel eluted with 20, 30, 40, 50, 75 and 100% ethyl acetate in hexanes. Yield 228 mg, 84%; HPLC (60/40) 3.57 minutes (98%); PBMS 410 (MH+, 100%);

Workup

  1. customthe product purified by chromatography on silica gel
  2. washeluted with 20, 30, 40, 50, 75 and 100% ethyl acetate in hexanes
  3. customHPLC (60/40) 3.57 minutes (98%)

Sources & evidence

ORD record
ord-e423d65ed7fa43f8b2d8e73ee4614b54
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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