Dimethylamine → HCID 25230559, compound

HRID 1961714Notes

Reaction equation

HRID 1961714 reaction equation
CS(Cl)(=O)=O.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]2[C:15]([CH2:27]O)=[N:16][CH:17]=[C:18]([N:20]3[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[N:21]3)[N:19]=2)=[CH:9][CH:8]=1.[CH2:29]([N:31](CC)[CH2:32]C)C.CNC>ClCCl.O1CCCC1.C(OCC)(=O)C.O>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]2[C:15]([CH2:27][N:31]([CH3:32])[CH3:29])=[N:16][CH:17]=[C:18]([N:20]3[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[N:21]3)[N:19]=2)=[CH:9][CH:8]=1

Participants

9

Reactant 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59570676HCID 59570676, compound

Product 1

HCID 25230559HCID 25230559, compoundYield 82%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methanesulfonyl chloride (274, 0.35 mmol) was added to a solution of [3-(4-chloro-phenylamino)-5-(3,5-dimethyl-pyrazol-1-yl)-pyrazin-2-yl]-methanol (58 mg, 0.18 mmol) and triethylamine (75 μL, 0.53 mmol) in dichloromethane (5 mL) and tetrahydrofuran (1 mL) and stirred for 15 minutes. Dimethylamine (2M in tetrahydrofuran, 1.32 mL, 2.64 mmol) was added and the solution was stirred overnight. Water and ethyl acetate were added and the organic solvents were evaporated in vacuo. The remaining aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulphate, filtrated and evaporated to give the crude product as a brown oil. Purification by flash chromatography (dichloromethane/methanol as eluent) gave (4-chloro-phenyl)-[3-dimethylaminomethyl-6-(3,5-dimethyl-pyrazol-1-yl)-pyrazin-2-yl]-amine (52 mg, 82%) as a brown solid.

Workup

  1. stirringthe solution was stirred overnight
  2. customthe organic solvents were evaporated in vacuo
  3. extractionThe remaining aqueous phase was extracted with ethyl acetate
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltrated
  7. customevaporated
  8. customto give the crude product as a brown oil
  9. customPurification by flash chromatography (dichloromethane/methanol as eluent)

Sources & evidence

ORD record
ord-d708cacb9c874747bde6e4492b709203
Source dataset
uspto-grants-2013_04
Patent number
US08415358B2

Reaction notes

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