Triethylamine → {4-[4-(1-Benzyl-3,5-dimethyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-3'-yl]-phenyl}-methanol hydrochloride

HRID 220573

반응식

HRID 220573 반응식
[ClH:1].Cl.[N:3]1([C:9]2[C:14]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17][CH:16]=3)=[N:13][CH:12]=[CH:11][N:10]=2)[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[CH2:23]([N:30]1[C:34]([CH3:35])=[C:33]([CH:36]=O)[C:32]([CH3:38])=[N:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl-].[NH4+]>ClC(Cl)C.C(=O)(O)[O-].[Na+].CO.C(O)(=O)C>[ClH:1].[CH2:23]([N:30]1[C:34]([CH3:35])=[C:33]([CH2:36][N:6]2[CH2:7][CH2:8][N:3]([C:9]3[C:14]([C:15]4[CH:16]=[CH:17][C:18]([CH2:21][OH:22])=[CH:19][CH:20]=4)=[N:13][CH:12]=[CH:11][N:10]=3)[CH2:4][CH2:5]2)[C:32]([CH3:38])=[N:31]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

참가 물질

10

반응물 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 9689341-Benzyl-3,5-dimethyl-1H-pyrazole-4-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68595263[4-(3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-3'-yl)-phenyl]-methanol dihydrochloride

생성물 1

HCID 68596468{4-[4-(1-Benzyl-3,5-dimethyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-3'-yl]-phenyl}-methanol hydrochloride수율 78%

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 887Methanol용매HCID 63651,1-Dichloroethane용매HCID 516892Sodium Bicarbonate용매

실험 절차

Combine [4-(3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-3′-yl)-phenyl]-methanol dihydrochloride (0.210 g, 0.612 mmol), 1-benzyl-3,5-dimethyl-1H-pyrazole-4-carbaldehyde (0.131 g, 0.612 mmol) and triethylamine (0.171 mL, 1.22 mmol) in dichloroethane (5 mL). Add glacial acetic acid (50 μL) followed by sodium triacetoxyborohydride (0.181 g, 0.856 mmol). Stir at room temperature for 3 days. 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 a yellow oil. Dissolve the oil in methanol and add ammonium chloride (1 equivalent) then sonicate the mixture for 10 min. Evaporate the solution to give the title compound as a yellow solid (0.241 g, 78%). MS (ES): m/z=469

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)
  7. customto give a yellow oil
  8. customthen sonicate the mixture for 10 min
  9. customEvaporate the solution

출처 및 근거

ORD 기록
ord-b37a47364e0b42e1a89168bef7fcbc5b
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202873B2

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