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

HRID 220496노트

반응식

HRID 220496 반응식
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

참가 물질

6

반응물 4

HCID 516892Sodium BicarbonateHCID 7365151,3,5-trimethyl-1H-pyrazole-4-carboxaldehyde2회HCID 5049666Sodium triacetoxyborohydrideHCID 866416583'-chloro-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl dihydrochloride

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-af4453e1839241e3ac030c158b6ad5dd
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202873B2

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