Pyridine → N-[3-(1H-benzimidazol-2-yl)-1-(2-trimethylsilanylethoxymethyl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide

HRID 25434

Reaction equation

HRID 25434 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([NH2:19])[CH:17]=2)[N:12]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[N:11]=1.N1C=CC=CC=1.[CH3:34][S:35]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[S:44](Cl)(=[O:46])=[O:45])(=[O:37])=[O:36]>C1CCCCC1.C(OCC)(=O)C>[NH:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:1]=[C:2]1[C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([NH:19][S:44]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=3[S:35]([CH3:34])(=[O:37])=[O:36])(=[O:46])=[O:45])[CH:17]=2)[N:12]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[N:11]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 27351782-Methanesulfonylbenzene-1-sulfonyl chlorideHCID 1363363453-(1H-benzimidazol-2-yl)-5-amino-1-{[2-(trimethylsilyl)ethoxy]methyl}indazole

Product 1

HCID 135621934N-[3-(1H-benzimidazol-2-yl)-1-(2-trimethylsilanylethoxymethyl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamideYield 94%

Reagents, catalysts & solvents 1

HCID 21867204Cyclohexane ethylacetateSolvent

Procedure

N-[3-(1H-Benzimidazol-2-yl)-1-(2-trimethylsilanylethoxymethyl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide can be obtained as described in Example 2 from 130 mg of 3-(1H-benzimidazol-2-yl)-1-(2-trimethylsilanylethoxymethyl)-1H-indazol-5-ylamine, 5 ml of pyridine and 87 mg of 2-methylsulfonylbenzenesulfonyl chloride. 192 mg of N-[3-(1H-benzimidazol-2-yl)-1-(2-trimethylsilanylethoxymethyl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide are thus obtained in the form of an orange lac (Rf=0.53, silica gel thin layer chromatography, eluent: cyclohexane/ethyl acetate (50/50 by volume), mass analysis: Cl: m/z 598 (M+H)+.)

Sources & evidence

ORD record
ord-2f8483c8059149e2b9e120ca1934177b
Source dataset
uspto-grants-2005_02
Patent number
US06858638B2

Linked notes

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