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 220573Notes

Reaction equation

HRID 220573 reaction equation
[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

Participants

10

Reactant 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

Product 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 hydrochlorideYield 78%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 63651,1-DichloroethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-b37a47364e0b42e1a89168bef7fcbc5b
Source dataset
uspto-grants-2012_06
Patent number
US08202873B2

Reaction notes

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