Methanesulfonyl chloride → HCID 59370325, compound

HRID 1848664Notes

Reaction equation

HRID 1848664 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-d0e29554446c48dab6ddbaa92409d984
Source dataset
uspto-grants-2015_02
Patent number
US08952161B2

Reaction notes

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