(Diethylamino)sulfur trifluoride → 6-(4-tert-butyl-phenyl)-2-fluoromethyl-5H-pyrazolo[1,5-a]pyrazin-4-one

HRID 2272977노트

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HRID 2272977 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:12][C:13](=[O:22])[C:14]3[N:15]([N:17]=[C:18]([CH2:20]O)[CH:19]=3)[CH:16]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(S(F)(F)[F:29])CC)C>ClCCl>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:12][C:13](=[O:22])[C:14]3[N:15]([N:17]=[C:18]([CH2:20][F:29])[CH:19]=3)[CH:16]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 717654606-(4-tert-butyl-phenyl)-2-hydroxymethyl-5H-pyrazolo[1,5-a]pyrazin-4-one

생성물 1

HCID 717650916-(4-tert-butyl-phenyl)-2-fluoromethyl-5H-pyrazolo[1,5-a]pyrazin-4-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-78 °C

실험 절차

A suspension of 149 mg (0.50 mmol) 6-(4-tert-butyl-phenyl)-2-hydroxymethyl-5H-pyrazolo[1,5-a]pyrazin-4-one in 1.25 ml dichloromethane is cooled to −78° C. Then 264 μl (2.00 mmol) diethylaminosulfurtrifluoride are added. The reaction mixture is allowed to reach room temperature over 30 minutes. The reaction mixture is evaporated and the residue is treated with water and saturated sodium hydrogen carbonate solution. The solids are filtered off and chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent to afford 6-(4-tert-butyl-phenyl)-2-fluoromethyl-5H-pyrazolo[1,5-a]pyrazin-4-one as white powder; HPLC/MS 2.80 min (B), [M+H] 300; 1H NMR (400 MHz, DMSO-d6) δ 11.57 (s, 1H), 8.03 (s, 1H), 7.73-7.64 (m, 2H), 7.55-7.46 (m, 2H), 7.15 (d, J=2.0 Hz, 1H), 5.52 (d, J=48.1 Hz, 2H), 1.32 (s, 9H).

후처리

  1. customThe reaction mixture is evaporated
  2. additionthe residue is treated with water and saturated sodium hydrogen carbonate solution
  3. filtrationThe solids are filtered off
  4. customchromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent

출처 및 근거

ORD 기록
ord-b2174e95f19a4d38af3e923d059b0948
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09120805B2

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