Triethylamine → Tert-butyl (tert-butoxycarbonyl{6-[(pyridin-3-ylsulfonyl)aminomethyl]pyridin-2-yl}amino)acetate

HRID 241292Notes

Reaction equation

HRID 241292 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([S:7](Cl)(=[O:9])=[O:8])[CH:2]=1.[C:11]([O:15][C:16](=[O:34])[CH2:17][N:18]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][NH2:33])[N:27]=1)[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C.S([O-])(O)(=O)=O.[K+]>C(Cl)Cl>[C:11]([O:15][C:16](=[O:34])[CH2:17][N:18]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][NH:33][S:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)(=[O:9])=[O:8])[N:27]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516920Potassium bisulfateHCID 3164136Pyridine-3-sulfonyl chlorideHCID 86651796Tert-butyl [(6-aminomethylpyridin-2-yl)tert-butoxycarbonylamino]acetate

Product 1

HCID 86651773Tert-butyl (tert-butoxycarbonyl{6-[(pyridin-3-ylsulfonyl)aminomethyl]pyridin-2-yl}amino)acetateYield 85.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-pyridylsulfonyl chloride (640 mg, 3.60 mmol) in methylene chloride (14 ml) were added tert-butyl[(6-aminomethylpyridin-2-yl)tert-butoxycarbonylamino]acetate (1.20 g, 3.56 mmol) obtained in Reference Example 12-(c) and triethylamine (2.24 ml, 16.2 mmol), followed by stirring at room temperature for 1 hour. After completion of the reaction, a 5% aqueous potassium hydrogensulfate solution was added to the reaction solution, followed by extraction with chloroform. The separated organic layer was washed sequentially with a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate=1:1→1:2 (V/V)), and fractions containing the desired compound were concentrated under reduced pressure to afford the title compound (1.45 g) as a colorless oil. (Yield: 85%)

Workup

  1. customAfter completion of the reaction
  2. extractionfollowed by extraction with chloroform
  3. washThe separated organic layer was washed sequentially with a saturated aqueous sodium hydrogencarbonate solution
  4. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additioncontaining the desired compound
  7. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-5c01bd12b82244b3b8c3849d2fb1e1bd
Source dataset
uspto-grants-2014_02
Patent number
US08648097B2

Reaction notes

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