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

HRID 1784898Notes

Reaction equation

HRID 1784898 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.C(=O)(O)[O-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[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

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 64841871-Isopropylpiperidine-4-Carboxylic AcidHCID 17856976HCID 17856976, compound

Product 1

HCID 101175564'-Bromo-2'-[(5-chloro-2-pyridyl)carbamoyl]-6'-hydroxy-1-isopropylpiperidine-4-carboxanilideYield 59.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Amino-5-bromo-N-(5-chloro-2-pyridyl)-3-hydroxybenzamide (5.14 g) and 2.83 g of 1-isopropylpiperidine-4-carboxylic acid were dissolved in 75 ml of N,N-dimethylformamide, then 4.33 g of 1-ethyl-3-dimethylaminopropylcarbodiimide hydrochloride and 3.04 g of 1-hydroxybenzotriazole were added thereto and the mixture was stirred at room temperature for 46 hours. The reaction solution was added to 750 ml of 1% aqueous solution of sodium bicarbonate and 200 ml of ethyl acetate were added thereto. Ethyl acetate was evaporated therefrom in vacuo and the resulting solid was collected by filtration and washed with water. The resulting solid was suspended in 100 ml of methanol and 10 ml of water and the suspension was stirred for one night. The resulting precipitate was collected by filtration and dried in vacuo to give 4.41 g of 4′-bromo-2′-[(5-chloro-2-pyridyl)carbamoyl]-6′-hydroxy-1-isopropylpiperidine-4-carboxanilide.

Workup

  1. additionwere added
  2. customEthyl acetate was evaporated
  3. filtrationin vacuo and the resulting solid was collected by filtration
  4. washwashed with water
  5. stirring10 ml of water and the suspension was stirred for one night
  6. filtrationThe resulting precipitate was collected by filtration
  7. customdried in vacuo

Sources & evidence

ORD record
ord-c6b5cc335d7c487e830aad2e34cfe502
Source dataset
uspto-grants-2009_03
Patent number
US07504417B2

Reaction notes

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