Indole-2-carboxylic acid → 1H-Indole-2-carboxylic acid [(1R)-(4-fluoro-benzyl)-2-(4-hydroxy-piperidin-1-yl)-2-oxo-ethyl]-amide

HRID 651141Notes

Reaction equation

HRID 651141 reaction equation
Cl.[NH2:2][C@H:3]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([F: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].[NH:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[C:22]1[C:30](O)=[O:31]>>[F:20][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][C@@H:3]([NH:2][C:30]([C:22]2[NH:21][C:29]3[C:24]([CH:23]=2)=[CH:25][CH:26]=[CH:27][CH:28]=3)=[O:31])[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 72899Indole-2-carboxylic acidHCID 67279148(R)-2-Amino-3-(4-fluoro-phenyl)-1-(4-hydroxy-piperidin-1-yl)-propan-1-one hydrochloride

Product 1

HCID 536349091H-Indole-2-carboxylic acid [(1R)-(4-fluoro-benzyl)-2-(4-hydroxy-piperidin-1-yl)-2-oxo-ethyl]-amide

Procedure

(R)-2-Amino-3-(4-fluoro-phenyl)-1-(4-hydroxy-piperidin-1-yl)-propan-1-one hydrochloride (0.5 mmol) and 1H-indole-2-carboxylic acid (0.5 mmol) were coupled according to Procedure A (0-25° C. reaction temperature) and the product purified by chromatography on silica gel eluted with 25, 30, 50, 75 and 80% ethyl acetate in hexanes. Yield 150 mg, 60%; HPLC (60/40) 3.66 minutes (97%); mp 204-207° C.; PBMS 410 (MH+, 100%);

Workup

  1. customthe product purified by chromatography on silica gel
  2. washeluted with 25, 30, 50, 75 and 80% ethyl acetate in hexanes
  3. customHPLC (60/40) 3.66 minutes (97%)

Sources & evidence

ORD record
ord-a2e29802d77449dcb4b178c83c5db158
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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