1-Hydroxybenzotriazole → 1-(6-Chloronaphthalene-2-sulfonyl)-4-(4-diisopropylaminomethyl-2-methoxybenzoyl)piperazine

HRID 278598Notes

Reaction equation

HRID 278598 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.[CH:22]([N:25]([CH2:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[C:32]([O:39][CH3:40])[CH:31]=1)[CH:26]([CH3:28])[CH3:27])([CH3:24])[CH3:23].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:34](=[O:35])[C:33]3[CH:37]=[CH:38][C:30]([CH2:29][N:25]([CH:26]([CH3:27])[CH3:28])[CH:22]([CH3:24])[CH3:23])=[CH:31][C:32]=3[O:39][CH3:40])[CH2:20][CH2:21]1)(=[O:14])=[O:15])[CH:7]=[CH:6]2

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 226279874-Diisopropylaminomethyl-2-methoxybenzoic acidHCID 227097661-(6-Chloronaphth-2-ylsulphonyl)piperazine hydrochloride

Product 1

HCID 226279571-(6-Chloronaphthalene-2-sulfonyl)-4-(4-diisopropylaminomethyl-2-methoxybenzoyl)piperazineYield 61.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 1-(6-chloronaphthalene-2-sulfonyl)piperazine hydrochloride(100 mg), 4-diisopropylaminomethyl-2-methoxybenzoic acid (77 mg), triethylamine (35 mg) and HOBt (43 mg) in DMF (10 ml) was added WSC hydrochloride (61 mg) under ice-cooling, and the solution was stirred at room temperature for 4 hours and concentrated. To the residue were 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 (99 mg).

Workup

  1. temperaturecooling
  2. concentrationconcentrated
  3. additionTo the residue were 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-5b81db15f67e4df78287ac04b92003ac
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Reaction notes

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