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

HRID 929911노트

반응식

HRID 929911 반응식
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

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 312751,4-DioxaneHCID 178457882HCID 178457882, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-5ea791708718482c9a2b365a9070ff73
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296725B2

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