Sodium Bicarbonate → 3'-Chloro-4-(1,3,5-trimethyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazine

HRID 220496ノート

反応式

HRID 220496 の反応式
Cl.Cl.[Cl:3][C:4]1[C:5]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[N:6][CH:7]=[CH:8][N:9]=1.[CH3:16][N:17]1[C:21]([CH3:22])=[C:20]([CH:23]=O)[C:19]([CH3:25])=[N:18]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>O1CCCC1>[Cl:3][C:4]1[C:5]([N:10]2[CH2:11][CH2:12][N:13]([CH2:23][C:20]3[C:19]([CH3:25])=[N:18][N:17]([CH3:16])[C:21]=3[CH3:22])[CH2:14][CH2:15]2)=[N:6][CH:7]=[CH:8][N:9]=1

参加物

6

反応物 4

HCID 516892Sodium BicarbonateHCID 7365151,3,5-trimethyl-1H-pyrazole-4-carboxaldehyde2 回HCID 5049666Sodium triacetoxyborohydrideHCID 866416583'-chloro-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl dihydrochloride

生成物 1

HCID 866416593'-Chloro-4-(1,3,5-trimethyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of 3′-chloro-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl dihydrochloride (2.11 g, 7.77 mmol, 1 eq) in tetrahydrofuran (20 mL) add 1,3,5-trimethyl-1H-pyrazole-4-carbaldehyde (1.61 g, 11.65 mmol, 1.5 eq). Stir for 10 min and add sodium triacetoxyborohydride (4.20 g, 19.40 mmol, 2.5 eq) in one portion. Stir at room temperature under nitrogen for 1 hr., then add further 1,3,5-trimethyl-1H-pyrazole-4-carbaldehyde (0.50 g, 3.6 mmol, 0.47 eq). Stir for 30 min., add saturated aqueous sodium hydrogen carbonate (100 mL) slowly, and then extract with DCM (3×50 mL). Pass the combined DCM extracts through an IST Phase Separator Frit®, concentrate and purify (silica gel chromatography, eluting with 2:98 to 5:95 methanol:DCM), to give the title preparation as a white powder (2.468 g, 98%). MS (ES): m/z=321 [M+H]+.

後処理

  1. stirringStir at room temperature under nitrogen for 1 hr
  2. stirringStir for 30 min.
  3. extractionextract with DCM (3×50 mL)
  4. concentrationconcentrate
  5. custompurify
  6. wash(silica gel chromatography, eluting with 2:98 to 5:95 methanol:DCM)
  7. customto give the title

出典と根拠

ORDレコード
ord-af4453e1839241e3ac030c158b6ad5dd
出典データセット
uspto-grants-2012_06
特許番号
US08202873B2

反応ノート

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