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

Reaktionsgleichung

Reaktionsgleichung von HRID 220573
[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

Komponenten

10

Edukt 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

Produkt 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 hydrochlorideAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 63651,1-DichloroethaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

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

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b37a47364e0b42e1a89168bef7fcbc5b
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202873B2

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