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Potassium Iodide → N-(2-{(1S,2S)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl)-1-(4-methoxybenzyl)-3-methyl-1H-indazol-5-amine

HRID 1039094
ノート
印刷プレビュー

反応式

HRID 1039094 の反応式
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][C:13]([NH2:17])=[CH:14][CH:15]=3)[C:10]([CH3:18])=[N:9]2)=[CH:5][CH:4]=1.CC1C=CC(S(O[CH2:32][CH2:33][C@@H:34]2[CH2:36][C@@H:35]2[CH:37]2[CH2:42][CH2:41][N:40]([C:43]3[N:48]=[CH:47][C:46]([Cl:49])=[CH:45][N:44]=3)[CH2:39][CH2:38]2)(=O)=O)=CC=1.[I-].[K+]>C(#N)C.O>[Cl:49][C:46]1[CH:45]=[N:44][C:43]([N:40]2[CH2:41][CH2:42][CH:37]([C@H:35]3[CH2:36][C@H:34]3[CH2:33][CH2:32][NH:17][C:13]3[CH:12]=[C:11]4[C:16](=[CH:15][CH:14]=3)[N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:20][CH:19]=3)[N:9]=[C:10]4[CH3:18])[CH2:38][CH2:39]2)=[N:48][CH:47]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 4875Potassium IodideHCID 669270631-(4-methoxybenzyl)-3-methyl-1H-indazol-5-amineHCID 866661412-{(1S,2R)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl 4-methylbenzenesulfonate

生成物 1

HCID 67778018N-(2-{(1S,2S)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl)-1-(4-methoxybenzyl)-3-methyl-1H-indazol-5-amine

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 6342Acetonitrile溶媒

反応条件

温度
110 °C

実験手順

1-(4-methoxybenzyl)-3-methyl-1H-indazol-5-amine (51 mg, 0.34 mmol) from step 2 of this example, 2-{(1S,2R)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl 4-methylbenzenesulfonate from step 1 of Example 5 (75 mg, 0.17 mmol) and potassium iodide (3 mg, 0.017 mmol) combined and the solids slurried in acetonitrile. The slurry was reacted in the microwave with stirring for 80 minutes at 110° C. using normal power. The mixture was cooled to RT, diluted with 4:1 water:saturated sodium bicarbonate (40 ml), extracted with EtOAc (3×40 ml), the organic fractions combined, washed with brine, dried over Na2SO4, filtered and the volatiles removed in vacuum. The product was purified by chromatography on SiO2 eluting with 10% acetone:DCM to give the titled compound.

後処理

  1. customThe slurry was reacted in the microwave
  2. temperatureThe mixture was cooled to RT
  3. extractionsaturated sodium bicarbonate (40 ml), extracted with EtOAc (3×40 ml)
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe volatiles removed in vacuum
  8. customThe product was purified by chromatography on SiO2 eluting with 10% acetone

出典と根拠

ORDレコード
ord-781ad068dea24ff4a1e3c261ea99c3c4
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08552022B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート