Methanesulfonyl chloride → HCID 56602985, compound

HRID 1620310Notes

Reaction equation

HRID 1620310 reaction equation
C[Si](C)(C)N[Si](C)(C)C.[Li].[Cl:11][C:12]1[CH:35]=[CH:34][C:15]([O:16][C:17]2[CH:25]=[CH:24][C:20]([C:21]([NH2:23])=[O:22])=[CH:19][C:18]=2[C:26]2[C:31]([O:32][CH3:33])=[CH:30][CH:29]=[CH:28][N:27]=2)=[CH:14][CH:13]=1.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>C1COCC1>[Cl:11][C:12]1[CH:35]=[CH:34][C:15]([O:16][C:17]2[CH:25]=[CH:24][C:20]([C:21]([NH:23][S:37]([CH3:36])(=[O:39])=[O:38])=[O:22])=[CH:19][C:18]=2[C:26]2[C:31]([O:32][CH3:33])=[CH:30][CH:29]=[CH:28][N:27]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 57426343Lithium bis(trimethylsilyl)amideHCID 66667011HCID 66667011, compound

Product 1

HCID 56602985HCID 56602985, compoundYield 5.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hexamethyldisilazane (1.5 mL, 1.55 mmol) was added to a solution of 4-(4-chlorophenoxy)-3-(3-methoxypyridin-2-yl)benzamide (Preparation 11, 0.184 g, 0.52 mmol) in THF (10 mL) and then the mixture was stirred at room temperature for 10 minutes. Methansulfonyl chloride (0.14 mL, 1.81 mmol) was added to the yellow solution and the mixture was stirred at room temperature for 18 hours. The reaction was quenched by the addition of aqueous ammonium chloride (10 mL) and extracted with DCM (3×30 mL). The organic layer was washed with water (2×30 mL), dried over magnesium sulfate, and concentrated in vacuo to afford the crude product (0.294 g). The crude material was purified by preparative A-HPLC to afford the title compound (12.2 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 18 hours
  2. customThe reaction was quenched by the addition of aqueous ammonium chloride (10 mL)
  3. extractionextracted with DCM (3×30 mL)
  4. washThe organic layer was washed with water (2×30 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto afford the crude product (0.294 g)
  8. customThe crude material was purified by preparative A-HPLC

Sources & evidence

ORD record
ord-d3ed72582ee64fe7a25ac0083a4ee9bc
Source dataset
uspto-grants-2014_07
Patent number
US08772343B2

Reaction notes

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