Methanesulfonyl chloride → HCID 59370325, compound

HRID 1486018Notes

Reaction equation

HRID 1486018 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:22]=[C:21]([Cl:23])[C:20]([C:24]2[CH:25]=[N:26][C:27]([C:32]([F:35])([F:34])[F:33])=[CH:28][C:29]=2[C:30]#[N:31])=[CH:19][C:6]=1[C:7]([N:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH3:18])[CH3:10])=[O:8].[CH3:36][S:37](Cl)(=[O:39])=[O:38].CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:23][C:21]1[C:20]([C:24]2[CH:25]=[N:26][C:27]([C:32]([F:35])([F:34])[F:33])=[CH:28][C:29]=2[C:30]#[N:31])=[CH:19][C:6]([C:7]([N:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])[CH3:10])=[O:8])=[C:5]([O:4][CH2:3][CH2:2][NH:1][S:37]([CH3:36])(=[O:39])=[O:38])[CH:22]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 68603631HCID 68603631, compound

Product 1

HCID 59370325HCID 59370325, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2-amino-ethoxy)-4-chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-N-(2-methoxy-phenyl)-N-methyl-benzamide (30 mg, 0.06 mmol) in DCM (1 mL), methanesulfonylchloride (7 μL, 0.09 mmol) and DIPEA (16 μL, 0.09 mmol) were added. The mixture was stirred at rt overnight, concentrated, diluted with 1 mL MeOH and purified by prep HPLC yielding 4-chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-(2-methanesulfonylamino-ethoxy)-N-(2-methoxy-phenyl)-N-methyl-benzamide 48-1. MS: 583.0 (M+H)+, tR=7.61 min (method 2).

Workup

  1. concentrationconcentrated
  2. additiondiluted with 1 mL MeOH
  3. custompurified by prep HPLC

Sources & evidence

ORD record
ord-88a6831185294402a8bc179d463a347a
Source dataset
uspto-grants-2016_08
Patent number
US09422310B2

Reaction notes

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