Methanesulfonyl chloride → HCID 86691636, compound

HRID 624325Notes

Reaction equation

HRID 624325 reaction equation
[CH2:1]([NH:3][C:4]1[C:24]([C:25]2[CH:26]=[CH:27][C:28]([O:43][CH3:44])=[C:29]([CH:42]=2)[C:30]([NH:32][C:33]2([C:36]3[N:41]=[CH:40][CH:39]=[CH:38][N:37]=3)[CH2:35][CH2:34]2)=[O:31])=[CH:23][C:7]2[C:8]([C:18]3[NH:19][CH:20]=[CH:21][N:22]=3)=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[O:10][C:6]=2[CH:5]=1)[CH3:2].[CH3:45][S:46](Cl)(=[O:48])=[O:47]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C.O>[CH2:1]([N:3]([C:4]1[C:24]([C:25]2[CH:26]=[CH:27][C:28]([O:43][CH3:44])=[C:29]([CH:42]=2)[C:30]([NH:32][C:33]2([C:36]3[N:41]=[CH:40][CH:39]=[CH:38][N:37]=3)[CH2:35][CH2:34]2)=[O:31])=[CH:23][C:7]2[C:8]([C:18]3[N:19]([S:46]([CH3:45])(=[O:48])=[O:47])[CH:20]=[CH:21][N:22]=3)=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=3)[O:10][C:6]=2[CH:5]=1)[S:46]([CH3:45])(=[O:48])=[O:47])[CH3:2]

Participants

6

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 71657866HCID 71657866, compound

Product 1

HCID 86691636HCID 86691636, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a solution of 5-(6-(ethylamino)-2-(4-fluorophenyl)-3-(1H-imidazol-2-yl)benzofuran-5-yl)-2-methoxy-N-(1-(pyrimidin-2-yl)cyclopropyl)benzamide (40 mg, 0.068 mmol) in pyridine (3.0 mL) at room temperature was added DMAP (16.60 mg, 0.136 mmol) followed by methanesulfonyl chloride (7.94 μl, 0.102 mmol). The reaction mixture was stirred at rt overnight, and then diluted with water. The mixture was extracted with EtOAc, and the organic extract washed with brine, dried over Na2SO4 and concentrated to obtain the title compound as an off white solid. Yield: 45 mg (89%). LCMS: (ES+) m/z=745.2 (M+H)+; Column—ACE Excel 2 C18 (50×3.0 mm-2 μm); M phase A: 2% MeCN-98% H2O-10 mM NH4COOH; M phase B: 98% MeCN-2% H2O-10 mM NH4COOH

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. extractionthe organic extract
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3ea808894e87406c8cc5c6569170ccbf
Source dataset
uspto-grants-2016_04
Patent number
US09303020B2

Reaction notes

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