Methanesulfonyl chloride → 2-[(4-tert-butylbenzyl)amino]-1-(5-isoquinolinyl)-2-oxoethyl Methanesulfonate

HRID 586052Notes

Reaction equation

HRID 586052 reaction equation
[C:1]([C:5]1[CH:26]=[CH:25][C:8]([CH2:9][NH:10][C:11](=[O:24])[CH:12]([OH:23])[C:13]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:14]=2[CH:15]=[CH:16][N:17]=[CH:18]3)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:27][S:28](Cl)(=[O:30])=[O:29]>N1C=CC=CC=1>[CH3:27][S:28]([O:23][CH:12]([C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[CH:15]=[CH:16][N:17]=[CH:18]2)[C:11]([NH:10][CH2:9][C:8]1[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:26][CH:25]=1)=[O:24])(=[O:30])=[O:29]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 11291000N-(4-tert-butylbenzyl)-2-hydroxy-2-(5-isoquinolinyl)acetamide

Product 1

HCID 574338452-[(4-tert-butylbenzyl)amino]-1-(5-isoquinolinyl)-2-oxoethyl Methanesulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The product from Example 277B (1.00 g, 2.87 mmol) in pyridine (5 mL) was treated with methanesulfonyl chloride (5.56 μL, 7.17 mmol). After stirring for 30 minutes, the mixture was concentrated under reduced pressure and diluted with CH2Cl2 (50 mL). The organic layer was washed with water (50 mL×3), dried (Na2SO4), filtered, and the filtrate concentrated under reduce pressure to provide the title compound. MS (ESI+) m/z 427 (M+H)+; MS (ESI−) m/z 425 (M−H)−; 1H NMR (DMSO, 300 MHz) δ 1.27 (s, 9H), 2.37 (s, 3H), 4.27 (dq, J1 14.9, J2 6.1, 2H), 6.84 (s, 1H), 7.17 (d, J 8.5, 2H), 7.38 (d, J 8.5, 2H), 8.07 (m, 2H), 8.37 (d, J 8.1, 1H), 8.60 (d, J 6.1, 1H), 8.97 (m, 1H), 9.21 (t, J 6.1, 1H), 9.96 (s, 1H).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additiondiluted with CH2Cl2 (50 mL)
  3. washThe organic layer was washed with water (50 mL×3)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-999262e316c74ea38d68ffdf5bf17378
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Reaction notes

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