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

HRID 220572Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 220572
[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:25]1[CH:29]=[C:28]([CH:30]=O)[CH:27]=[N:26]1)[CH3:24].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:25]1[CH:29]=[C:28]([CH2:30][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)[CH:27]=[N:26]1)[CH3:24]

Komponenten

10

Edukt 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 27589001-Ethyl-1H-pyrazole-4-carboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68595263[4-(3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-3'-yl)-phenyl]-methanol dihydrochloride

Produkt 1

HCID 68595506{4-[4-(1-Ethyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-3'-yl]-phenyl}-methanol hydrochlorideAusbeute 83,1 %

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 (0.177 g, 0.516 mmol), 1-ethyl-1H-pyrazole-4-carbaldehyde (0.064 g, 0.516 mmol) and triethylamine (0.144 mL, 1.03 mmol) in dichloroethane (4 mL). Add glacial acetic acid (42 mL) followed by sodium triacetoxyborohydride (0.153 g, 0.722 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 a white solid. Dissolve the solid 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 white solid (0.178 g, 83%). MS (ES): m/z=379

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 white solid
  8. customthen sonicate the mixture for 10 min
  9. customEvaporate the solution

Quellen und Nachweise

ORD-Eintrag
ord-01fb991012494ad28fc6df9defbb02b9
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202873B2

Notizen zur Reaktion

Wird geladen…