Methanesulfonyl chloride → HCID 54592022, compound

HRID 2276757Notes

Reaction equation

HRID 2276757 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]([CH2:18][C:19]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)([CH3:21])[CH3:20])C(=O)OC(C)(C)C)=[N:8][CH:9]=1.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>C1COCC1>[F:28][C:25]1[CH:26]=[CH:27][C:22]([C:19]([CH3:21])([CH3:20])[CH2:18][NH:10][C:7]2[N:8]=[CH:9][C:4]([CH2:3][CH2:2][NH:1][S:30]([CH3:29])(=[O:32])=[O:31])=[CH:5][CH:6]=2)=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 68234621HCID 68234621, compound

Product 1

HCID 54592022HCID 54592022, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 20 dram vial was added tert-butyl 5-(2-aminoethyl)pyridin-2-yl(2-(4-fluorophenyl)-2-methylpropyl)carbamate (140 mg, 0.34 mmol, 1.0 equiv), TEA (87 μL, 0.67 mmol, 2.0 equiv, THF (3 mL), and methanesulfonyl chloride (29 μL, 0.37 mmol, 1.1 equiv). The reaction was stirred for 2 h and then concentrated, followed by the addition of MeOH (1 mL) and 4N HCl/dioxane (3 mL). The reaction was stirred for 1 h, concentrated, and then purified by preparative TLC (5% MeOH/CH2Cl2) to give 5 mg of N-(2-(6-(2-(4-fluorophenyl)-2-methylpropylamino)pyridin-3-yl)ethyl)-methanesulfonamide (m/z [M+H]=366).

Workup

  1. concentrationconcentrated
  2. additionfollowed by the addition of MeOH (1 mL) and 4N HCl/dioxane (3 mL)
  3. stirringThe reaction was stirred for 1 h
  4. concentrationconcentrated
  5. custompurified by preparative TLC (5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-44e5e2c985214ae1be4f6ee908fd2d82
Source dataset
uspto-grants-2015_09
Patent number
US09133123B2

Reaction notes

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