1-Hydroxybenzotriazole → 4'-Bromo-2'-[(5-chloro-2-pyridyl)carbamoyl]-6'-hydroxy-1-isopropylpiperidine-4-carboxanilide hydrochloride

HRID 1784901Notes

Reaction equation

HRID 1784901 reaction equation
[NH2:1][C:2]1[C:17]([OH:18])=[CH:16][C:15]([Br:19])=[CH:14][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][N:8]=1)=[O:5].[CH:20]([N:23]1[CH2:28][CH2:27][CH:26]([C:29](O)=[O:30])[CH2:25][CH2:24]1)([CH3:22])[CH3:21].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C)C=O.C(OCC)(=O)C.O.C(N(CC)CC)C>[ClH:13].[Br:19][C:15]1[CH:16]=[C:17]([OH:18])[C:2]([NH:1][C:29]([CH:26]2[CH2:27][CH2:28][N:23]([CH:20]([CH3:22])[CH3:21])[CH2:24][CH2:25]2)=[O:30])=[C:3]([C:4](=[O:5])[NH:6][C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][N:8]=2)[CH:14]=1

Participants

9

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 64841871-Isopropylpiperidine-4-Carboxylic AcidHCID 178569762-amino-5-bromo-N-(5-chloro-2-pyridyl)-3-hydroxybenzamide

Product 1

HCID 179649144'-Bromo-2'-[(5-chloro-2-pyridyl)carbamoyl]-6'-hydroxy-1-isopropylpiperidine-4-carboxanilide hydrochlorideYield 72.7%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Amino-5-bromo-N-(5-chloro-2-pyridyl)-3-hydroxybenzamide (2.39 g) and 1.32 g of 1-isopropylpiperidine-4-carboxylic acid were dissolved in 35 ml of N,N-dimethylformamide, then 2.02 g of 1-ethyl-3-dimethylaminopropylcarbodiimide hydrochloride, 1.42 g of 1-hydroxybenzotriazole and 1.46 ml of triethylamine were added thereto and the mixture was stirred at room temperature for 22 hours. To the reaction solution were added 105 ml of water and 105 ml of ethyl acetate, the mixture was stirred at room temperature for 3 hours and the resulting precipitate was filtered, washed with ethyl acetate and water and dried in vacuo. The resulting solid was suspended in 60 ml of ethanol, 5 ml of 1N hydrochloric acid were added thereto and the mixture was stirred at room temperature for 30 hours. The resulting precipitate was filtered, washed with ethanol and dried in vacuo to give 1.35 g of 4′-bromo-2′-[(5-chloro-2-pyridyl)carbamoyl]-6′-hydroxy-1-isopropylpiperidine-4-carboxanilide hydrochloride.

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. filtrationthe resulting precipitate was filtered
  3. washwashed with ethyl acetate and water
  4. customdried in vacuo
  5. addition5 ml of 1N hydrochloric acid were added
  6. stirringthe mixture was stirred at room temperature for 30 hours
  7. filtrationThe resulting precipitate was filtered
  8. washwashed with ethanol
  9. customdried in vacuo

Sources & evidence

ORD record
ord-a7e9fbe4f20a4ac4afc9bb11f2d35b06
Source dataset
uspto-grants-2009_03
Patent number
US07504417B2

Reaction notes

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