Hydrochloric Acid → HCID 22144685, compound

HRID 1825007Notes

Reaction equation

HRID 1825007 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].N1C=CC=CC=1.Cl.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]2[N:24]([CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=3[F:47])[C:25]3[C:30]([CH:31]=2)=[CH:29][C:28]([NH:32][C:33](=O)[CH2:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:27][CH:26]=3)=[O:22])=[CH:16][CH:15]=1.Cl>ClCCl>[CH3:36][C:35]([CH3:38])([CH3:37])[CH2:34][CH2:33][NH:32][C:28]1[CH:29]=[C:30]2[C:25](=[CH:26][CH:27]=1)[N:24]([CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1[F:47])[C:23]([C:21]([NH:20][C:17]1[CH:18]=[CH:19][C:14]([NH:13][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:15][CH:16]=1)=[O:22])=[CH:31]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 22144664HCID 22144664, compound

Product 1

HCID 22144685HCID 22144685, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

22.5 mg (0.20 mmol) of methanesulphonyl chloride are dissolved in 1 ml of dichloromethane, and 38.9 mg (0.49 mmol) of pyridine are added. A solution of 100 mg (0.20 mmol) of N-(4-aminophenyl)-5-[(3,3-dimethylbutyl)amino]-1-(2-fluorobenzyl)-1H-indole-2-carboxamide hydrochloride (Example 57) in 1 ml of dichloromethane is added dropwise to this mixture, and the reaction mixture is stirred at RT overnight. For work-up, 22 ml of 1-molar hydrochloric acid are added, and the mixture is extracted repeatedly with dichloromethane. The combined organic phases are washed in each case once with saturated copper sulphate solution, saturated sodium bicarbonate solution and water. They are then dried over sodium sulphate and filtered, and the solvent is removed under reduced pressure. This gives 96.2 mg (73%) of the product.

Workup

  1. extractionthe mixture is extracted repeatedly with dichloromethane
  2. washThe combined organic phases are washed in each case once with saturated copper sulphate solution, saturated sodium bicarbonate solution and water
  3. dry with materialThey are then dried over sodium sulphate
  4. filtrationfiltered
  5. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-d035c1d823284436b7d44ce0a54a8cef
Source dataset
uspto-grants-2006_05
Patent number
US07045544B2

Reaction notes

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