Acetic Anhydride → HCID 25230629, compound

HRID 1961721Notes

Reaction equation

HRID 1961721 reaction equation
[NH2:1][CH2:2][C:3]1[C:4]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[N:5][C:6]([N:9]2[C:13]([CH3:14])=[CH:12][C:11]([CH3:15])=[N:10]2)=[CH:7][N:8]=1.C(N(CC)CC)C.[C:31](OC(=O)C)(=[O:33])[CH3:32].C(=O)([O-])O.[Na+]>ClCCl>[Cl:23][C:20]1[CH:19]=[CH:18][C:17]([NH:16][C:4]2[C:3]([CH2:2][NH:1][C:31](=[O:33])[CH3:32])=[N:8][CH:7]=[C:6]([N:9]3[C:13]([CH3:14])=[CH:12][C:11]([CH3:15])=[N:10]3)[N:5]=2)=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 25230564HCID 25230564, compound

Product 1

HCID 25230629HCID 25230629, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[3-Aminomethyl-6-(3,5-dimethyl-pyrazol-1-yl)-pyrazin-2-yl ]-(4-chloro-phenyl)-amine (40 mg, 0.12 mmol), triethylamine (19 μL, 0.13 mmol) and dichloromethane (2 mL) was cooled on an ice bath. Acetic anhydride (12 μM, 0.12 mmol) was added and the mixture was stirred for 45 min. Aqueous sodium hydrogen carbonate was added and the aqueous phase was extracted with ethyl acetate (3×). The combined organic phases were dried over sodium sulphate, filtrated and concentrated in vacuo. The crude product was purified by flash chromatography (dichloromethane/methanol as eluent) to give N-[3-(4-chloro-phenylamino)-5-(3,5-dimethyl -pyrazol-1-yl)-pyrazin-2-ylmethyl]-acetamide (29 mg, 64%) as a white solid. Mp. 228-230° C. LC-ESI-HRMS of [M+H]+ shows 371.1404 Da. Calc. 371.138712 Da, dev. 4.5 ppm

Workup

  1. extractionthe aqueous phase was extracted with ethyl acetate (3×)
  2. dry with materialThe combined organic phases were dried over sodium sulphate
  3. filtrationfiltrated
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash chromatography (dichloromethane/methanol as eluent)

Sources & evidence

ORD record
ord-76cf9e6233f9402ea9dcfd1dcd8d7dbf
Source dataset
uspto-grants-2013_04
Patent number
US08415358B2

Reaction notes

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