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

HRID 887320Notes

Reaction equation

HRID 887320 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-03af48a22e1f4ce599654af40bcaabfb
Source dataset
uspto-grants-2012_08
Patent number
US08247413B2

Reaction notes

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