Sodium Hydroxide → HCID 68595558, compound

HRID 220541

Reaction equation

HRID 220541 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([N:14]3[CH2:19][CH2:18][N:17]([CH2:20][C:21]4[CH:22]=[N:23][NH:24][CH:25]=4)[CH2:16][CH2:15]3)=[N:10][CH:11]=[CH:12][N:13]=2)=[CH:4][CH:3]=1.[OH-].[Na+].[ClH:28].[Cl:29][CH2:30][CH2:31][NH:32][CH3:33].[Cl-].[NH4+]>C(#N)C.S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.CO>[ClH:29].[ClH:28].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([N:14]3[CH2:19][CH2:18][N:17]([CH2:20][C:21]4[CH:25]=[N:24][N:23]([CH2:30][CH2:31][NH:32][CH3:33])[CH:22]=4)[CH2:16][CH2:15]3)=[N:10][CH:11]=[CH:12][N:13]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 3028223Ethanamine, 2-chloro-N-methyl-, hydrochloride (1:1)HCID 59321743HCID 59321743, compound

Product 1

HCID 68595558HCID 68595558, compoundYield 23%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

Dissolve 3′-(4-fluoro-phenyl)-4-(1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (0.450 g, 1.33 mmol) in acetonitrile (3 mL) and add solid sodium hydroxide (0.186 g, 4.65 mmol). After 30 min. add (2-chloro-ethyl)-methyl-amine hydrochloride (0.190 g, 1.46 mmol) and tetrabutylammonium bisulfate (18 mg, 0.0531 mmol) then reflux the mixture for 20 hr. Cool and filter the mixture then evaporate. Purify using silica gel chromatography, eluting with 6:94 2N ammonia in methanol:DCM to give a yellow oil. Dissolve the solid in methanol and add ammonium chloride then sonicate the mixture for 10 min. Evaporate the solution to give the title compound as a white solid (0.139 g, 23%). MS (ES): m/z=396 [M+H]+.

Workup

  1. temperaturethen reflux the mixture for 20 hr
  2. temperatureCool
  3. filtrationfilter the mixture
  4. customthen evaporate
  5. customPurify
  6. washeluting with 6:94 2N ammonia in methanol
  7. customDCM to give a yellow oil
  8. customthen sonicate the mixture for 10 min
  9. customEvaporate the solution

Sources & evidence

ORD record
ord-9fc5132842d847008eb03b8a484a7813
Source dataset
uspto-grants-2012_06
Patent number
US08202873B2

Linked notes

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