Diethyl Ether → HCID 9915451, compound

HRID 2298806Notes

Reaction equation

HRID 2298806 reaction equation
[NH2:1][CH2:2][C:3]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[C:11]([NH:12][C:13](=[O:35])[C:14]3[CH:19]=[CH:18][C:17]([C:20]([N:22]4[C:28]5[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=5[CH2:26][CH2:25][CH2:24][CH2:23]4)=[O:21])=[CH:16][C:15]=3[O:33][CH3:34])[C:5]=2[N:4]=1.[CH3:36][S:37](Cl)(=[O:39])=[O:38].CCOCC>N1C=CC=CC=1>[CH3:34][O:33][C:15]1[CH:16]=[C:17]([C:20]([N:22]2[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[CH2:26][CH2:25][CH2:24][CH2:23]2)=[O:21])[CH:18]=[CH:19][C:14]=1[C:13]([NH:12][C:11]1[C:5]2[N:4]=[C:3]([CH2:2][NH:1][S:37]([CH3:36])(=[O:39])=[O:38])[NH:7][C:6]=2[CH:8]=[CH:9][CH:10]=1)=[O:35]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 31297Methanesulfonyl chlorideHCID 9912514HCID 9912514, compound

Product 1

HCID 9915451HCID 9915451, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To an ice-bath-cooled solution of N-(2-aminomethyl-1H-benzimidazol-4-yl)-2-methoxy-4-(2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)carbonylbenzamide (100 mg) in pyridine (5 ml) was added methanesulfonyl chloride (24.4 mg) and the solution was stirred at room temperature for 4 hours. After removing the solvent by evaporation, the product was purified by silica gel column chromatography (chloroform) to give a syrup and the syrup was solidified with ether to give 2-methoxy-N-(2-methanesulfonylaminomethyl-1H-benzimidazol-4-yl)-4-(2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)carbonylbenzamide (98 mg).

Workup

  1. customAfter removing the solvent
  2. customby evaporation
  3. customthe product was purified by silica gel column chromatography (chloroform)
  4. customto give a syrup

Sources & evidence

ORD record
ord-e0b4715941e24e7abbb075d4ad10db56
Source dataset
uspto-grants-2002_12
Patent number
US06495542B1

Reaction notes

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