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

HRID 2272977ノート

反応式

HRID 2272977 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b2174e95f19a4d38af3e923d059b0948
出典データセット
uspto-grants-2015_09
特許番号
US09120805B2

反応ノート

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