Benzenesulfonyl chloride → HCID 178522498, compound

HRID 1367929Notes

Reaction equation

HRID 1367929 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:24](=[O:31])[NH:25][C:26]2[NH:27][CH:28]=[CH:29][N:30]=2)[C:5]2[N:9]=[C:8]([NH:10][C:11]([C:13]3[N:14]=[CH:15][C:16]4[C:21]([CH:22]=3)=[CH:20][CH:19]=[CH:18][CH:17]=4)=[O:12])[NH:7][C:6]=2[CH:23]=1.[C:32]1([S:38](Cl)(=[O:40])=[O:39])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>N1C=CC=CC=1.C(Cl)Cl.[Cl-].[Na+].O>[C:32]1([S:38]([NH:1][C:2]2[CH:3]=[C:4]([C:24](=[O:31])[NH:25][C:26]3[NH:27][CH:28]=[CH:29][N:30]=3)[C:5]3[NH:9][C:8]([NH:10][C:11]([C:13]4[N:14]=[CH:15][C:16]5[C:21]([CH:22]=4)=[CH:20][CH:19]=[CH:18][CH:17]=5)=[O:12])=[N:7][C:6]=3[CH:23]=2)(=[O:40])=[O:39])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 58724420HCID 58724420, compound

Product 1

HCID 178522498HCID 178522498, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

82 mg (0.2 mmol) of the isoquinoline-3-carboxylic acid [6-amino-4-(1H-imidazol-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-amide (See Example 130) was dissolve 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 r.t. for 2 h. Brine (5 mL) was added and stirred for 10 min. The resulting solid was collected, washed with water (3×2 mL) and ethyl acetate (3×3 mL) and dried to give 55 mg (50%) of isoquinoline-3-carboxylic acid [5-benzenesulfonylamino-7-(1H-imidazol-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-amide as a solid. LCMS: 553 (M+1)+.

Workup

  1. stirringstirred for 10 min
  2. customThe resulting solid was collected
  3. washwashed with water (3×2 mL) and ethyl acetate (3×3 mL)
  4. customdried

Sources & evidence

ORD record
ord-9de73b068ff94350bec16d9691b0cc97
Source dataset
uspto-grants-2011_02
Patent number
US07893267B2

Reaction notes

Loading…