1-Hydroxybenzotriazole → 1-[(6-Chloronaphthalen-2-yl)sulfonyl]-4-[4-(pyridin-4-yl)benzoyl]piperazine

HRID 278599Notes

Reaction equation

HRID 278599 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)(=[O:15])=[O:14])[CH:7]=[CH:6]2.[N:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:36]=[CH:35][C:31]([C:32](O)=[O:33])=[CH:30][CH:29]=2)=[CH:24][CH:23]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.C(N(CC)CC)C>[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([N:16]1[CH2:17][CH2:18][N:19]([C:32](=[O:33])[C:31]3[CH:30]=[CH:29][C:28]([C:25]4[CH:24]=[CH:23][N:22]=[CH:27][CH:26]=4)=[CH:36][CH:35]=3)[CH2:20][CH2:21]1)(=[O:14])=[O:15])[CH:7]=[CH:6]2

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 15208114-(Pyridin-4-yl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 227097661-(6-Chloronaphth-2-ylsulphonyl)piperazine hydrochloride

Product 1

HCID 99572891-[(6-Chloronaphthalen-2-yl)sulfonyl]-4-[4-(pyridin-4-yl)benzoyl]piperazineYield 95.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 1-(6-chloronaphthalene-2-sulfonyl)piperazine hydrochloride (90 mg), 4-(4-pyridyl)benzoic acid (52 mg), triethylamine (35 mg) and HOBt (39 mg) in DMF (10 ml) was added WSC hydrochloride (55 mg) under ice-cooling and the solution was stirred at room temperature 4 hours and concentrated. To the residue was added ethyl acetate and sodium bicarbonate solution. The organic layer was separated, washed with water, and extracted with 1 N hydrochloric acid. The extract was made alkaline with sodium hydroxide solution and extracted with dichloromethane. The extract was dried and concentrated, and the residue was crystallized with ether to give colorless crystals of the title compound (122 mg).

Workup

  1. temperaturecooling
  2. concentrationconcentrated
  3. additionTo the residue was added ethyl acetate and sodium bicarbonate solution
  4. customThe organic layer was separated
  5. washwashed with water
  6. extractionextracted with 1 N hydrochloric acid
  7. extractionextracted with dichloromethane
  8. customThe extract was dried
  9. concentrationconcentrated
  10. customthe residue was crystallized with ether

Sources & evidence

ORD record
ord-e2738ba0f8fa4ffe9e253ce5f59a3fe4
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Reaction notes

Loading…