Triethylamine → 3'-chloro-4-(1-ethyl-3-methyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl

HRID 220555노트

반응식

HRID 220555 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.[CH2:16]([N:18]1[CH:22]=[C:21]([CH:23]=O)[C:20]([CH3:25])=[N:19]1)[CH3:17].C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.C(=O)(O)[O-].[Na+].C(O)(=O)C>[Cl:3][C:4]1[C:5]([N:10]2[CH2:11][CH2:12][N:13]([CH2:23][C:21]3[C:20]([CH3:25])=[N:19][N:18]([CH2:16][CH3:17])[CH:22]=3)[CH2:14][CH2:15]2)=[N:6][CH:7]=[CH:8][N:9]=1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 5732031-ethyl-3-methyl-1H-pyrazole-4-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 866416583'-chloro-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl dihydrochloride

생성물 1

HCID 866416653'-chloro-4-(1-ethyl-3-methyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl수율 65%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 63651,1-Dichloroethane용매HCID 516892Sodium Bicarbonate용매

실험 절차

Combine 3′-chloro-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl dihydrochloride (2.21 g, 8.18 mmol), 1-ethyl-3-methyl-1H-pyrazole-4-carbaldehyde (1.3 g, 9.40 mmol) and triethylamine (1.31 mL, 9.40 mmol) in dichloroethane (50 mL). Add glacial acetic acid (0.85 mL) followed by sodium triacetoxyborohydride (2.99 g, 14.1 mmol). Stir at room temperature for 20 hr. Dilute with saturated aq. sodium bicarbonate then extract three times using DCM. Dry (sodium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 4.5:95.5 methanol (with 2 M ammonia):DCM), to give 3′-chloro-4-(1-ethyl-3-methyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl as a yellow oil (1.702 g, 65%). MS (ES): m/z=321 [M+H]+.

후처리

  1. extractionthen extract three times
  2. dry with materialDry (sodium sulfate)
  3. filtrationfilter
  4. concentrationconcentrate
  5. custompurify
  6. wash(silica gel chromatography, eluting with 4.5:95.5 methanol (with 2 M ammonia):DCM)

출처 및 근거

ORD 기록
ord-442138f678e14c09b20cd62562e58b2f
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202873B2

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