Triethylamine → 2-(Benzyloxy)-5-[(4-fluorophenyl)carbonyl]-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine

HRID 571730ノート

反応式

HRID 571730 の反応式
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH2:11]([O:18][C:19]1[CH:27]=[C:22]2[CH2:23][NH:24][CH2:25][CH2:26][N:21]2[N:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>[CH2:11]([O:18][C:19]1[CH:27]=[C:22]2[CH2:23][N:24]([C:6]([C:5]3[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=3)=[O:7])[CH2:25][CH2:26][N:21]2[N:20]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 867064922-(Benzyloxy)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine

生成物 1

HCID 725512832-(Benzyloxy)-5-[(4-fluorophenyl)carbonyl]-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine収率 83%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 10340Sodium Carbonate溶媒

実験手順

4-Fluorobenzoyl chloride (0.36 mL, 3.04 mmol) was added to a stirred solution of 2-(benzyloxy)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine (0.71 g, 2.53 mmol) and triethylamine (0.65 mL, 3.8 mmol) in DCM (25 mL) under nitrogen at 0° C. The mixture was stirred at room temperature for 16 hours, diluted with a saturated solution of Na2CO3 and extracted with DCM. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 20/80). The desired fractions were collected, the solvents evaporated in vacuo and the residue triturated with DIPE to yield 2-(benzyloxy)-5-[(4-fluorophenyl)carbonyl]-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine (0.73 g, 83% yield) as a white solid. C20H18FN3O2. 1H NMR (400 MHz, CDCl3) δ ppm 4.10 (br. s., 4H), 4.73 (br. s., 2 H), 5.18 (s, 2 H), 5.50 (br. s., 1 H), 7.10-7.19 (m, 2 H), 7.29-7.35 (m, 1 H), 7.35-7.41 (m, 2 H), 7.41-7.46 (m, 2 H), 7.46-7.51 (m, 2 H).

後処理

  1. extractionextracted with DCM
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvents evaporated in vacuo
  6. customThe crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 20/80)
  7. customThe desired fractions were collected
  8. customthe solvents evaporated in vacuo
  9. customthe residue triturated with DIPE

出典と根拠

ORDレコード
ord-0dbd249fa9bd48bb876d7eb4b253d53d
出典データセット
uspto-grants-2015_05
特許番号
US09029366B2

反応ノート

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