1-(2-Hydroxyethyl)piperazine → HCID 58046369、化合物

HRID 1035793ノート

反応式

HRID 1035793 の反応式
Cl[C:2]1[CH:3]=[C:4]([CH3:36])[C:5]2[N:6]([C:8]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]4[N:24]([S:27]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)(=[O:29])=[O:28])[CH:25]=[CH:26][C:19]=34)=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[N:10]=2)[N:7]=1.[OH:37][CH2:38][CH2:39][N:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1.C(N(CC)CC)C>C(O)CCCC.Cl>[F:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[N:10]=[C:5]3[C:4]([CH3:36])=[CH:3][C:2]([N:43]4[CH2:44][CH2:45][N:40]([CH2:39][CH2:38][OH:37])[CH2:41][CH2:42]4)=[N:7][N:6]3[C:8]=2[C:18]2[CH:23]=[CH:22][N:21]=[C:20]3[N:24]([S:27]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)(=[O:29])=[O:28])[CH:25]=[CH:26][C:19]=23)=[CH:12][CH:13]=1

参加物

6

反応物 3

HCID 76771-(2-Hydroxyethyl)piperazineHCID 8471TriethylamineHCID 468994996-chloro-2-(4-fluorophenyl)-8-methyl-3-[1-(phenylsulphonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]imidazo[1,2-b]pyridazine

生成物 1

HCID 58046369HCID 58046369、化合物収率 35.3%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 62761-Pentanol溶媒

反応条件

温度
150 °C

実験手順

A mixture of 0.530 g (1.02 mmol) of 6-chloro-2-(4-fluorophenyl)-8-methyl-3-[1-(phenylsulphonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]imidazo[1,2-b]pyridazine, prepared according to the method described in step 1.4 from Example 1, 0.266 g (2.05 mmol) of 1-(2-hydroxyethyl)piperazine (CAS 103-76-4) and 0.14 ml (1.0 mmol) of triethylamine in 5 ml of pentanol is stirred for 2 days at 150° C. The reaction medium is diluted with 20 ml of an aqueous solution of hydrochloric acid and the solution is washed with ethyl acetate. The aqueous phase is then basified by addition of aqueous ammonia and the product is extracted with dichloromethane. The organic phase is separated, dried over sodium sulphate and the solvent is removed by evaporation under reduced pressure. The brown oil obtained is then purified by chromatography on a silica gel column (40 g) by eluting with a mixture of dichloromethane, methanol and aqueous ammonia (95/5/0.5) in order to give 0.220 g of 2-{4-[2-(4-fluorophenyl)-8-methyl-3-{1-[phenylsulphonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}imidazo[1,2-b]pyridazin-6-yl]piperazin-1-yl}ethanol in the form of an amorphous powder which is used in the following step.

後処理

  1. customprepared
  2. washthe solution is washed with ethyl acetate
  3. additionThe aqueous phase is then basified by addition of aqueous ammonia
  4. extractionthe product is extracted with dichloromethane
  5. customThe organic phase is separated
  6. dry with materialdried over sodium sulphate
  7. customthe solvent is removed by evaporation under reduced pressure
  8. customThe brown oil obtained
  9. customis then purified by chromatography on a silica gel column (40 g)
  10. washby eluting with a mixture of dichloromethane, methanol and aqueous ammonia (95/5/0.5) in order

出典と根拠

ORDレコード
ord-918e66b490ba4866ae1f0a6c46acba92
出典データセット
uspto-grants-2013_10
特許番号
US08546395B2

反応ノート

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