Triethylamine → ((S)-2-{7-[(4-Acetylamino-benzenesulfonylamino)-methyl]-furo[2,3-g]indazol-1-yl}-1-methyl-ethyl)-carbamic acid benzyl ester

HRID 1453904Notes

Reaction equation

HRID 1453904 reaction equation
[CH2:1]([O:8][C:9](=[O:28])[NH:10][C@@H:11]([CH3:27])[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]3[O:24][C:23]([CH2:25][NH2:26])=[CH:22][C:20]3=2)[CH:15]=[N:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:36]([NH:39][C:40]1[CH:49]=[CH:48][C:43]([S:44](Cl)(=[O:46])=[O:45])=[CH:42][CH:41]=1)(=[O:38])[CH3:37].C(=O)(O)[O-].[Na+]>C1COCC1.O>[CH2:1]([O:8][C:9](=[O:28])[NH:10][C@@H:11]([CH3:27])[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]3[O:24][C:23]([CH2:25][NH:26][S:44]([C:43]4[CH:42]=[CH:41][C:40]([NH:39][C:36](=[O:38])[CH3:37])=[CH:49][CH:48]=4)(=[O:46])=[O:45])=[CH:22][C:20]3=2)[CH:15]=[N:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8481N-Acetylsulfanilyl chlorideHCID 516892Sodium BicarbonateHCID 68858114[(S)-2-(7-Aminomethyl-furo[2,3-g]indazol-1-yl)-1-methylethyl]-carbamic acid benzyl ester

Product 1

HCID 68855404((S)-2-{7-[(4-Acetylamino-benzenesulfonylamino)-methyl]-furo[2,3-g]indazol-1-yl}-1-methyl-ethyl)-carbamic acid benzyl esterYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product from Example 17, Step B (0.32 g, 0.85 mmol) in THF (10 mL) containing triethylamine (3.39 mmol, 0.47 mL) was cooled (ice bath) and N-acetylsulfanilyl chloride (0.20 g, 0.85 mmol) was added followed by stirring for one hour. The reaction mixture was warmed to room temperature, water (1 mL) was added, and stirring continued until all the solids dissolved. Saturated aqueous sodium bicarbonate (150 mL) was added and the mixture was extracted with ethyl acetate (2×100 mL). The combined extracts were washed with brine (100 mL), dried (MgSO4) and evaporated to a residue which was purified by chromatography (silica gel, hexane/ethyl acetate gradient) to give an amorphous solid (0.32 g, 66%): LC/MS m/z 576 [M+H]+.

Workup

  1. additionwas added
  2. stirringstirring
  3. dissolutiondissolved
  4. extractionthe mixture was extracted with ethyl acetate (2×100 mL)
  5. washThe combined extracts were washed with brine (100 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated to a residue which
  8. customwas purified by chromatography (silica gel, hexane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-80149dcbc8e84e1cab98960bfb68bdfb
Source dataset
uspto-grants-2009_01
Patent number
US07476687B2

Reaction notes

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