Benzenesulfonyl chloride → HCID 178522493, compound

HRID 1910271Notes

Reaction equation

HRID 1910271 reaction equation
[NH2:1][C:2]1[C:10]2[N:9]=[C:8]([NH:11][C:12]([C:14]3[N:15]=[CH:16][C:17]4[C:22]([CH:23]=3)=[CH:21][CH:20]=[CH:19][CH:18]=4)=[O:13])[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:24]1([S:30](Cl)(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>N1C=CC=CC=1.C(Cl)Cl.[Cl-].[Na+].O>[C:24]1([S:30]([NH:1][C:2]2[C:10]3[NH:9][C:8]([NH:11][C:12]([C:14]4[N:15]=[CH:16][C:17]5[C:22]([CH:23]=4)=[CH:21][CH:20]=[CH:19][CH:18]=5)=[O:13])=[N:7][C:6]=3[CH:5]=[CH:4][CH:3]=2)(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 66940303HCID 66940303, compound

Product 1

HCID 178522493HCID 178522493, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

66 mg (0.2 mmol) of isoquinoline-3-carboxylic acid (4-amino-1H-benzoimidazol-2-yl)-amide was dissolved in pyridine (0.6 mL). To this stirred solution at 0° C., 0.2 mmol of phenylsulfonyl chloride in 0.2 mL of DCM was added in one portion. The reaction mixture was stirred at room temperature for 2 h. Brine (5 mL) was added and stirred for 10 min. The resulting solid was collected by filtration, washed with water (3×2 ml) and EtOAc (3×3 mL) and dried to yield 46 mg (52%) of isoquinoline-3-carboxylic acid (7-benzenesulfonylamino-1H-benzoimidazol-2-yl)-amide. LCMS: 444 (M+1)+.

Workup

  1. stirringstirred for 10 min
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with water (3×2 ml) and EtOAc (3×3 mL)
  4. customdried

Sources & evidence

ORD record
ord-6aabc94165c74dcc8893a3d0909f59e6
Source dataset
uspto-grants-2013_12
Patent number
US08598353B2

Reaction notes

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