2-Thiophenesulfonyl chloride → {n-[3-(1h-Indol-2-yl)-1h-indazol-5-yl]}thiophene-2-sulfonamide

HRID 25440

反応式

HRID 25440 の反応式
I[C:2]1([C:27](OC(C)(C)C)=O)[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N:11]([S:19]([C:22]3[S:23][CH:24]=[CH:25][CH:26]=3)(=[O:21])=[O:20])C(OC(C)(C)C)=O)[CH:9]=2)[N:4]=[N:3]1.N[C:35]1[CH:36]=[C:37]2[C:41](=[CH:42][CH:43]=1)[NH:40]N=[C:38]2I.S1C=CC=C1S(Cl)(=O)=O.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>>[NH:40]1[C:41]2[C:37](=[CH:36][CH:35]=[CH:43][CH:42]=2)[CH:38]=[C:27]1[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][S:19]([C:22]3[S:23][CH:24]=[CH:25][CH:26]=3)(=[O:20])=[O:21])[CH:9]=2)[NH:4][N:3]=1

参加物

5

反応物 4

HCID 855182-Thiophenesulfonyl chlorideHCID 90495Di-tert-butyl dicarbonateHCID 22567122Tert-butyl 3-iodo-5-(n-tert-butoxycarbonyl-2-thiophenesulfonylamino)indazolecarboxylateHCID 178507363HCID 178507363、化合物

生成物 1

HCID 135855049{n-[3-(1h-Indol-2-yl)-1h-indazol-5-yl]}thiophene-2-sulfonamide

実験手順

tert-Butyl 3-iodo-5-(N-tert-butoxycarbonyl-2-thiophenesulfonylamino)-indazolecarboxylate can be prepared as described in Example 85 using 2 g of 5-amino-3-iodo-1H-indazole and 1.61 g of thiophene-2-sulfonyl chloride. The intermediate crude is purified by flash chromatography (98/2 by volume dichloromethane/methanol), resulting in 2.30 g of an orangey solid, which is then treated with 3.71 g of di-tert-butyl dicarbonate according to the procedure. After purification by flash chromatography (eluent:dichloromethane), 3.15 g of tert-butyl 3-iodo-5-(N-tert-butoxycarbonyl-2-thiophenesulfonylamino)indazolecarboxylate are obtained in the form of a white solid melting at 163° C. (LC/MS analysis: Tr=4.34 minutes; [M+H]+=605.93; [M+H]+-tert-butyl=549.90).

後処理

  1. customThe intermediate crude is purified by flash chromatography (98/2 by volume dichloromethane/methanol)
  2. customresulting in 2.30 g of an orangey solid, which
  3. customAfter purification by flash chromatography (eluent:dichloromethane), 3.15 g of tert-butyl 3-iodo-5-(N-tert-butoxycarbonyl-2-thiophenesulfonylamino)indazolecarboxylate

出典と根拠

ORDレコード
ord-eb485f0229fc4601a63bfa1f3a95ed9d
出典データセット
uspto-grants-2005_02
特許番号
US06858638B2

関連ノート

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