Acetonitrile → 4-[2-(3-Isopropyl-phenylamino)-1-methyl-1H-benzoimidazol-5-yloxy]-pyridine-2-carboxylic acid (2-phenylmethanesulfonylamino-ethyl)-amide

HRID 1915686

Reaction equation

HRID 1915686 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[CH:12]=[C:11]([O:13][C:14]2[CH:33]=[CH:32][C:17]3[N:18]([CH3:31])[C:19]([NH:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([CH:28]([CH3:30])[CH3:29])[CH:23]=4)=[N:20][C:16]=3[CH:15]=2)[CH:10]=[CH:9][N:8]=1)=[O:6].C([O-])([O-])=O.[K+].[K+].C(#N)C.[C:43]1([CH2:49][S:50](Cl)(=[O:52])=[O:51])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>O>[C:43]1([CH2:49][S:50]([NH:1][CH2:2][CH2:3][NH:4][C:5]([C:7]2[CH:12]=[C:11]([O:13][C:14]3[CH:33]=[CH:32][C:17]4[N:18]([CH3:31])[C:19]([NH:21][C:22]5[CH:27]=[CH:26][CH:25]=[C:24]([CH:28]([CH3:30])[CH3:29])[CH:23]=5)=[N:20][C:16]=4[CH:15]=3)[CH:10]=[CH:9][N:8]=2)=[O:6])(=[O:52])=[O:51])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 74740Phenylmethanesulfonyl chlorideHCID 210373234-[2-(3-Isopropyl-phenylamino)-1-methyl-1H-benzo-imidazol-5-yloxy]-pyridine-2-carboxylic acid (2-amino-ethyl)-amide

Product 1

HCID 220412414-[2-(3-Isopropyl-phenylamino)-1-methyl-1H-benzoimidazol-5-yloxy]-pyridine-2-carboxylic acid (2-phenylmethanesulfonylamino-ethyl)-amide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture containing 4-[2-(3-Isopropyl-phenylamino)-1-methyl-1H-benzoimidazol-5-yloxy]-pyridine-2-carboxylic acid (2-amino-ethyl)-amide (1 eq) (prepared using previously described example 3), K2CO3 (5 eq), (0.2 M in a 5:1 mixture of acetonitrile and water) were added α-toluenesulfonyl chloride (1 eq) via syringe. The resulting heterogeneous mixture was allowed to stir for 1 hour at room temperature. The mixture was then diluted with water and extracted with dichloromethane. The organics were washed with water and a saturated solution of sodium chloride, dried with sodium sulfate and concentrated in vacuo to viscous oil. Purification by chromatography yielded 4-[2-(3-Isopropyl-phenylamino)-1-methyl-1H-benzoimidazol-5-yloxy]-pyridine-2-carboxylic acid (2-phenylmethanesulfonylamino-ethyl)-amide. MS: MH+599

Workup

  1. customprepared
  2. extractionextracted with dichloromethane
  3. washThe organics were washed with water
  4. dry with materiala saturated solution of sodium chloride, dried with sodium sulfate
  5. concentrationconcentrated in vacuo to viscous oil
  6. customPurification by chromatography

Sources & evidence

ORD record
ord-d12b642e94b64c6fb7c469e9f5192450
Source dataset
uspto-grants-2013_12
Patent number
US08614330B2

Linked notes

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