Diisopropylethylamine → [6-Bromo-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-[4-(piperidine-1-sulfonyl)-piperazin-1-yl]-methanone

HRID 1786451

反応式

HRID 1786451 の反応式
Cl.[Br:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([C:12](O)=[O:13])[NH:9]2)=[CH:5][C:4]=1[O:15][CH:16]1[CH2:21][CH2:20][N:19]([CH:22]([CH3:24])[CH3:23])[CH2:18][CH2:17]1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[N:47]1([S:53]([N:56]2[CH2:61][CH2:60][NH:59][CH2:58][CH2:57]2)(=[O:55])=[O:54])[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]1.C(N(CC)C(C)C)(C)C.C(=O)(O)[O-].[Na+]>CN(C)C=O>[Br:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([C:12]([N:59]3[CH2:58][CH2:57][N:56]([S:53]([N:47]4[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52]4)(=[O:55])=[O:54])[CH2:61][CH2:60]3)=[O:13])[NH:9]2)=[CH:5][C:4]=1[O:15][CH:16]1[CH2:21][CH2:20][N:19]([CH:22]([CH3:23])[CH3:24])[CH2:18][CH2:17]1

参加物

7

反応物 5

HCID 81531DiisopropylethylamineHCID 2855011-(1-Piperidinylsulfonyl)piperazineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 670179306-bromo-5-(1-isopropyl-piperidin-4-yloxy)-1H-indole-2-carboxylic acid hydrochloride

生成物 1

HCID 68565981[6-Bromo-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-[4-(piperidine-1-sulfonyl)-piperazin-1-yl]-methanone収率 56%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 0.5 g (1.20 mmol) 6-bromo-5-(1-isopropyl-piperidin-4-yloxy)-1H-indole-2-carboxylic acid hydrochloride in 8 mL N,N-dimethylformamide, 0.48 g (1.50 mmol) O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate, 0.31 g (1.33 mmol) 1-(piperidin-1-yl-sulfonyl)-piperazine and 1.0 mL (0.77 g, 6.0 mmol) N,N-diisopropylethylamine were added. After 2 h the solution was poured on 10% aqueous sodium bicarbonate solution, the phases were separated and the aqueous phase was extracted three times with ethyl acetate. The combined organic layers were washed three times with water followed by brine, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash chromatography twice on silica gel using a gradient of dichloromethane: methanol (100:0 to 50:50 v/v) as eluant, to afford 0.4 g (56%) of the title compound as a light-yellow foam.

後処理

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted three times with ethyl acetate
  3. washThe combined organic layers were washed three times with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash chromatography twice on silica gel using a gradient of dichloromethane: methanol (100:0 to 50:50 v/v) as eluant

出典と根拠

ORDレコード
ord-1e436c8e703f4c7799339d289b3f6850
出典データセット
uspto-grants-2009_03
特許番号
US07507736B2

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