4-Chlorobenzenesulfonyl chloride → (3-{[(4-Chloro-benzenesulfonyl)-(4-pyrazol-1-yl-benzyl)-amino]-methyl}-phenoxy)-acetic acid tert-butyl ester

HRID 2300528Notes

Reaction equation

HRID 2300528 reaction equation
[C:1]([O:5][C:6](=[O:29])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH:28]=[CH:27][CH:26]=[N:25]3)=[CH:20][CH:19]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=1.C(N(CC)CC)C.NCCN(CCN)CCN>C(Cl)Cl>[C:1]([O:5][C:6](=[O:29])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]([S:37]([C:34]2[CH:35]=[CH:36][C:31]([Cl:30])=[CH:32][CH:33]=2)(=[O:39])=[O:38])[CH2:17][C:18]2[CH:19]=[CH:20][C:21]([N:24]3[CH:28]=[CH:27][CH:26]=[N:25]3)=[CH:22][CH:23]=2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 73984-Chlorobenzenesulfonyl chloride2×HCID 8471Triethylamine2×HCID 77731Tris(2-aminoethyl)amineHCID 54338479{3-[(4-Pyrazol-1-yl-benzylamino)-methyl]-phenoxy}-acetic acid tert-butyl ester

Product 1

HCID 53952039(3-{[(4-Chloro-benzenesulfonyl)-(4-pyrazol-1-yl-benzyl)-amino]-methyl}-phenoxy)-acetic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of {3-[(4-pyrazol-1-yl-benzylamino)-methyl]-phenoxy}-acetic acid tert-butyl ester (15 mg, 0.038 mmol), prepared in Step A of Example 13a, 4-chlorobenzenesulfonyl chloride (5 eq), and triethylamine (5 eq) in CH2Cl2 (1-2 mL) was stirred at room temperature for 72 h. Additional 4-chlorobenzenesulfonyl chloride (5 eq) and triethylamine (5 eq) were added and the reaction was stirred for 24 h followed by addition of tris(2-aminoethyl)amine on polymer support. The reaction was stirred for 24 h and the resin was removed by filtration with the aid of CH2Cl2. The organic solution was washed sequentially with 5.5% aqueous HCl and saturated NaHCO3 solution. The organic solution was concentrated and was used in Step B without further purification.

Workup

  1. stirringthe reaction was stirred for 24 h
  2. stirringThe reaction was stirred for 24 h
  3. customthe resin was removed by filtration with the aid of CH2Cl2
  4. washThe organic solution was washed sequentially with 5.5% aqueous HCl and saturated NaHCO3 solution
  5. concentrationThe organic solution was concentrated
  6. customwas used in Step B without further purification

Sources & evidence

ORD record
ord-0632a344faf74e0abb349ef636000f77
Source dataset
uspto-grants-2002_12
Patent number
US06498172B1

Reaction notes

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