Acetic Acid → 2-[4-(3'-Chloro-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-ylmethyl)-pyrazol-1-yl]-ethanol

HRID 220497Notes

Reaction equation

HRID 220497 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][N:7]=1.[OH:14][CH2:15][CH2:16][N:17]1[CH:21]=[C:20]([CH:22]=O)[CH:19]=[N:18]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl>[Cl:1][C:2]1[C:3]([N:8]2[CH2:9][CH2:10][N:11]([CH2:22][C:20]3[CH:19]=[N:18][N:17]([CH2:16][CH2:15][OH:14])[CH:21]=3)[CH2:12][CH2:13]2)=[N:4][CH:5]=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 140864382-Chloro-3-(piperazin-1-yl)pyrazineHCID 247026081-(2-hydroxyethyl)-1H-pyrazole-4-carbaldehyde

Product 1

HCID 594382452-[4-(3'-Chloro-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-ylmethyl)-pyrazol-1-yl]-ethanol

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 3′-chloro-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (0.789 g, 4.01 mmol) and 1-(2-hydroxy-ethyl)-1H-pyrazole-4-carbaldehyde (0.562 g, 4.01 mmol) in DCE (35 mL) add sodium triacetoxyborohydride (1.28 g, 6.02 mmol) and acetic acid (0.382 mL) and stir at room temperature for 20 hr. Add saturated aqueous sodium bicarbonate, separate the layers, extract the aqueous layer twice with DCM, dry (sodium sulfate), filter and concentrate. Purify using silica gel chromatography, eluting with 6:94 methanol (with 2N ammonia):DCM to give the title preparation as a yellow oil (1.16 g, 90%). MS (ES): m/z=323 [M+H]+.

Workup

  1. customAdd saturated aqueous sodium bicarbonate, separate the layers
  2. extractionextract the aqueous layer twice with DCM
  3. dry with materialdry (sodium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify
  7. washeluting with 6:94 methanol (with 2N ammonia)
  8. customDCM to give the title

Sources & evidence

ORD record
ord-f4b0616a3dd54133a21a60d3c954edd2
Source dataset
uspto-grants-2012_06
Patent number
US08202873B2

Reaction notes

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