Triethylamine → HCID 25230627, compound

HRID 1961717Notes

Reaction equation

HRID 1961717 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:10]=[C:11]([N:17]3[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[N:18]3)[C:12]([CH2:15][OH:16])=[N:13][CH:14]=2)=[CH:4][CH:3]=1.[CH2:24](N(CC)CC)C.CS(Cl)(=O)=O.C[O-].[Na+]>O1CCCC1.[Cl-].[Na+].O.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]2[CH:14]=[N:13][C:12]([CH2:15][O:16][CH3:24])=[C:11]([N:17]3[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[N:18]3)[N:10]=2)=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10942334Sodium MethoxideHCID 59570663HCID 59570663, compound

Product 1

HCID 25230627HCID 25230627, compoundYield 9.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of [5-(4-chloro-phenylamino)-3-(3,5-dimethyl -pyrazol-1-yl)-pyrazin-2-yl]-methanol (50 mg, 0.15 mmol) and triethyl amine (0.06 mL, 0.45 mmol) in tetrahydrofuran (5 mL) was added methanesulfonyl chloride (0.23 mL, 0.30 mmol) and the solution was stirred for 15 min. Sodium methoxide (30 5 in methanol, 0.85 mL, 4.5 mmol) was added and the mixture was stirred for 1.5 hour. Water (20 mL) and brine (30 mL) was added and the qquosus phase was extracted with ethyl acetate. The combined organic phases were dried over magnesium sulphate, filtrated and concentrated in vacuo. The crude product was purified by flash chromatography to give (4-chloro-phenyl)-[6-(3,5-dimethyl-pyrazol-1-yl)-5-methoxymethyl-pyrazin-2-yl]-amine (5 mg, 8%) as an orange solid. Mp. 147-151° C. LC-ESI-HRMS of [M+Na]+ shows 366.1087 Da. Calc. 366.109788 Da, dev. −3 ppm

Workup

  1. stirringthe mixture was stirred for 1.5 hour
  2. extractionthe qquosus phase was extracted with ethyl acetate
  3. dry with materialThe combined organic phases were dried over magnesium sulphate
  4. filtrationfiltrated
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-f2b2d93364b646f3bf72f7c443c4f208
Source dataset
uspto-grants-2013_04
Patent number
US08415358B2

Reaction notes

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