Triethylamine → (3-{[(4-Pyrazol-1-yl-benzyl)-(5-pyridin-2-yl-thiophene-2-sulfonyl)-amino]-methyl}-phenoxy)-acetic acid tert-butyl ester

HRID 2300529Notes

Reaction equation

HRID 2300529 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].[N:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[C:36]1[S:40][C:39]([S:41](Cl)(=[O:43])=[O:42])=[CH:38][CH:37]=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]([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)[S:41]([C:39]2[S:40][C:36]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][N:30]=3)=[CH:37][CH:38]=2)(=[O:42])=[O:43])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 77731Tris(2-aminoethyl)amineHCID 27372315-(2-Pyridyl)thiophene-2-sulfonyl chloride2×HCID 54338479{3-[(4-Pyrazol-1-yl-benzylamino)-methyl]-phenoxy}-acetic acid tert-butyl ester

Product 1

HCID 54362284(3-{[(4-Pyrazol-1-yl-benzyl)-(5-pyridin-2-yl-thiophene-2-sulfonyl)-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, 5-pyridin-2-yl-thiophene-2-sulfonyl chloride (5 eq), and triethylamine (5 eq), in CH2Cl2 (1-2 mL) was stirred at room temperature for 72 h. Additional 5-pyridin-2-yl-thiophene-2-sulfonyl 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 CH2Cl. 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 CH2Cl
  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-ec0bd86313924e12a18af65a12e47467
Source dataset
uspto-grants-2002_12
Patent number
US06498172B1

Reaction notes

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