Hydrochloric Acid → 5-Chloro-1H-indole-2-carboxylic acid [2-(4-hydroxy-piperidin-1-yl)-2-oxo-ethyl]-amide

HRID 1872106Notes

Reaction equation

HRID 1872106 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[Cl:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18]([NH:20][CH2:21][C:22](O)=[O:23])=[O:19])=[CH:12]2.CN(C)C=O.ClCCl.Cl>C(OCC)(=O)C>[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:22](=[O:23])[CH2:21][NH:20][C:18]([C:13]2[NH:14][C:15]3[C:11]([CH:12]=2)=[CH:10][C:9]([Cl:8])=[CH:17][CH:16]=3)=[O:19])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 79341Piperidin-4-olHCID 11436686N-[(5-chloro-1H-indol-2-yl)carbonyl]glycineHCID 22350042dichloromethane N,N-dimethylformamide

Product 1

HCID 155210155-Chloro-1H-indole-2-carboxylic acid [2-(4-hydroxy-piperidin-1-yl)-2-oxo-ethyl]-amide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Hydroxypiperidine (0.83 mmol) and [(5-chloro-1H-indole-2-carbonyl)-amino]-acetic acid (0.8 mmol) were coupled according to procedure A (dimethylformamide- dichloromethane reaction solvent) with the following workup: the reaction mixture was stirred with ethyl acetate and aqueous 2N HCl, the resulting suspension filtered and the collected solid washed successively with aqueous 2N HCl, aqueous 2N NaOH, ether and dried : Yield 180 mg, 68%; TSPMS 336/338 (MH+, 100%);

Workup

  1. filtrationthe resulting suspension filtered
  2. washthe collected solid washed successively with aqueous 2N HCl, aqueous 2N NaOH, ether
  3. customdried

Sources & evidence

ORD record
ord-aedf34d0714d453ab42df8659f1f123e
Source dataset
uspto-grants-2000_08
Patent number
US06107329

Reaction notes

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