2-Pyrazinecarboxylic acid → HCID 69341671, compound

HRID 219727Notes

Reaction equation

HRID 219727 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.[C:10]([C:14]1[N:19]=[C:18]([N:20]2[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][CH2:28][CH2:29][NH2:30])[CH2:22][CH2:21]2)[CH:17]=[C:16]([CH:31]2[CH2:34][CH2:33][CH2:32]2)[N:15]=1)([CH3:13])([CH3:12])[CH3:11].C(N(C(C)C)CC)(C)C.OC1C2N=NNC=2C=CC=1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[C:10]([C:14]1[N:19]=[C:18]([N:20]2[CH2:21][CH2:22][N:23]([CH2:26][CH2:27][CH2:28][CH2:29][NH:30][C:7]([C:2]3[CH:3]=[N:4][CH:5]=[CH:6][N:1]=3)=[O:9])[CH2:24][CH2:25]2)[CH:17]=[C:16]([CH:31]2[CH2:34][CH2:33][CH2:32]2)[N:15]=1)([CH3:13])([CH3:11])[CH3:12]

Participants

7

Reactant 5

HCID 10472-Pyrazinecarboxylic acidHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 690260674-[4-(2-tert-Butyl-6-cyclobutyl-pyrimidin-4-yl)piperazin-1-yl]-butylamineHCID 178418300HCID 178418300, compound

Product 1

HCID 69341671HCID 69341671, compoundYield 55.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.28 g of 2-pyrazinecarboxylic acid (2.26 mmol) and 0.78 g of 4-[4-(2-tert-butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-butylamine (2.27 mmol) were dissolved in 30 ml of dichloromethane. Addition of 1.19 g of diisopropylethylamine (9.26 mmol), 0.155 g of hydroxybenzotriazole (HOBt, 1.15 mmol), and 0.487 g of N-ethyl-N′-(3-dimethyl-aminopropyl)-carbodiimide hydrochloride (EDCl, 2.54 mmol) at 0° C. was followed by stirring for 16 h at room temperature. After the addition of 0.24 g of N-ethyl-N′-(3-dimethylaminopropyl)-carbodiimide hydrochloride the mixture was stirred for further 4 h. 50 ml of dichloromethane were added. The organic layer was washed with water and saturated aqueous sodium chloride. The dichloromethane phase was dried over magnesium sulfate, filtered, and concentrated to dryness. The crude product was purified by chromatography on silica gel using ethyl acetate and ethyl acetate-methanol (5%). Evaporation of the solvent yielded 0.568 g of the title compound as a white solid.

Workup

  1. stirringwas stirred for further 4 h
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride
  3. dry with materialThe dichloromethane phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe crude product was purified by chromatography on silica gel
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-5811b6b181e84042ad5df227bc7c3a2f
Source dataset
uspto-grants-2012_06
Patent number
US08202868B2

Reaction notes

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