Hydrochloric Acid → 2-(4-(4-chloropyrimidin-2-ylamino)-1H-pyrazol-1-yl)-N-isopropylacetamide

HRID 929911ノート

反応式

HRID 929911 の反応式
O[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:10]=[N:11][N:12]([CH2:14][C:15]([NH:17][CH:18]([CH3:20])[CH3:19])=[O:16])[CH:13]=2)[N:3]=1.Cl.O1CCOCC1.O=P(Cl)(Cl)[Cl:30]>C(#N)C>[Cl:30][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:10]=[N:11][N:12]([CH2:14][C:15]([NH:17][CH:18]([CH3:20])[CH3:19])=[O:16])[CH:13]=2)[N:3]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 312751,4-DioxaneHCID 178457882HCID 178457882、化合物

生成物 1

HCID 900240272-(4-(4-chloropyrimidin-2-ylamino)-1H-pyrazol-1-yl)-N-isopropylacetamide

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a mixture of 2-(4-(4-hydroxypyrimidin-2-ylamino)-1H-pyrazol-1-yl)-N-isopropylacetamide (6.0 g, 22 mmol) in acetonitrile (300 mL) was added 4M HCl in dioxane (12 mL, 48 mmol) then POCl3 (10 g). The mixture was heated to reflux for 0.5 h then concentrated in vacuo. The residue was slurried with water and adjusted to pH 9 with aqueous sodium hydrogen carbonate. The remaining solid was collected by filtration and purified by column chromatography (50% v/v DCM/ethyl acetate) to afford 2-(4-(4-chloropyrimidin-2-ylamino)-1H-pyrazol-1-yl)-N-isopropylacetamide II-1 (2.30 g, 36%) as a white solid. LC-MS (Method A), RT=8.28 min. (ES+) 295.

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 0.5 h
  3. concentrationthen concentrated in vacuo
  4. filtrationThe remaining solid was collected by filtration
  5. custompurified by column chromatography (50% v/v DCM/ethyl acetate)

出典と根拠

ORDレコード
ord-5ea791708718482c9a2b365a9070ff73
出典データセット
uspto-grants-2016_03
特許番号
US09296725B2

反応ノート

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