Methanesulfonyl chloride → HCID 20634984, compound

HRID 460392Notes

Reaction equation

HRID 460392 reaction equation
Cl.Cl.Cl.Cl.[NH2:5][C:6]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([C:14]2[CH:15]=[CH:16][C:17]([N:20]3[CH2:26][CH2:25][CH2:24][N:23]([C:27]4[CH:32]=[CH:31][C:30]([C:33]5[CH:38]=[C:37]([O:39][CH3:40])[C:36]([NH2:41])=[C:35]([O:42][CH3:43])[CH:34]=5)=[CH:29][N:28]=4)[CH2:22][CH2:21]3)=[N:18][CH:19]=2)=[CH:8][C:7]=1[O:44][CH3:45].[CH3:46][S:47](Cl)(=[O:49])=[O:48]>N1C=CC=CC=1>[CH3:46][S:47]([NH:5][C:6]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([C:14]2[CH:15]=[CH:16][C:17]([N:20]3[CH2:26][CH2:25][CH2:24][N:23]([C:27]4[CH:32]=[CH:31][C:30]([C:33]5[CH:38]=[C:37]([O:39][CH3:40])[C:36]([NH:41][S:47]([CH3:46])(=[O:49])=[O:48])=[C:35]([O:42][CH3:43])[CH:34]=5)=[CH:29][N:28]=4)[CH2:22][CH2:21]3)=[N:18][CH:19]=2)=[CH:8][C:7]=1[O:44][CH3:45])(=[O:49])=[O:48]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 20634926HCID 20634926, compound

Product 1

HCID 20634984HCID 20634984, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1,4-bis[5-(4-amino-3,5-dimethoxyphenyl)-2-pyridyl]hexahydro-1,4-diazepine tetrahydrochloride (40.0 mg, 0.0570 mmol), which was synthesized in Example 34, in pyridine (1.0 mL) was added methanesulfonyl chloride (30.0 mg, 0.260 mmol). The reaction mixture was stirred for 15 minutes, and concentrated under reduced pressure. A solution of the residue in methanol-chloroform (1:10) was washed with saturated aqueous sodium hydrogencarbonate and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was recrystallized from chloroform-hexane to yield the title compound as a pale brown crystalline powder (melting point: 235.0–239.0° C.) (28.0 mg, yield: 68%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. washA solution of the residue in methanol-chloroform (1:10) was washed with saturated aqueous sodium hydrogencarbonate and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from chloroform-hexane

Sources & evidence

ORD record
ord-6f0fd8b50be64dacab832646beddd26a
Source dataset
uspto-grants-2007_03
Patent number
US07196101B2

Reaction notes

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