Triethylamine → N-(2-{4-[3'-(4-Fluoro-phenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-ylmethyl]-pyrazol-1-yl}-ethyl)-N-methyl-methanesulfonamide hydrochloride

HRID 220542Notes

Reaction equation

HRID 220542 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][N:24]([CH2:26][CH2:27][NH:28][CH3:29])[CH:25]=4)[CH2:16][CH2:15]3)=[N:10][CH:11]=[CH:12][N:13]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:37][S:38]([Cl:41])(=[O:40])=[O:39].[Cl-].[NH4+]>C(Cl)Cl.C(=O)(O)[O-].[Na+].CO>[ClH:41].[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][N:24]([CH2:26][CH2:27][N:28]([CH3:29])[S:38]([CH3:37])(=[O:40])=[O:39])[CH:25]=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 8471TriethylamineHCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 59321877HCID 59321877, compound

Product 1

HCID 68596214N-(2-{4-[3'-(4-Fluoro-phenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-ylmethyl]-pyrazol-1-yl}-ethyl)-N-methyl-methanesulfonamide hydrochlorideYield 97%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

Dissolve (2-{4-[3′-(4-fluoro-phenyl)-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-ylmethyl]-pyrazol-1-yl}-ethyl)-methyl-amine (0.124 g, 0.314 mmol) in DCM (3 mL) with triethylamine (66 μL, 0.470 mmol). Add methanesulfonyl chloride (26 μL, 0.329 mmol) dropwise in DCM (1 mL). Stir the mixture for 20 hr. Dilute with saturated aqueous sodium bicarbonate then extract 3 times with DCM. Dry (sodium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 4.5:95.5 2 M ammonia in methanol:DCM), to give a yellow oil. Dissolve the oil in methanol and add ammonium chloride then sonicate the mixture for 10 min. Evaporate the solution to give the title compound as a yellow solid (0.154 g, 97%). MS (ES): m/z=474 [M+H]+.

Workup

  1. extractionthen extract 3 times with DCM
  2. dry with materialDry (sodium sulfate)
  3. filtrationfilter
  4. concentrationconcentrate
  5. custompurify
  6. wash(silica gel chromatography, eluting with 4.5:95.5 2 M ammonia in methanol:DCM)
  7. customto give a yellow oil
  8. customthen sonicate the mixture for 10 min
  9. customEvaporate the solution

Sources & evidence

ORD record
ord-0b1465dc6009492884cef2e16580b014
Source dataset
uspto-grants-2012_06
Patent number
US08202873B2

Reaction notes

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