Aminopyrazine → HCID 59436366, compound

HRID 1961411Notes

Reaction equation

HRID 1961411 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH2:7].C([Mg]Cl)(C)C.[F:13][C:14]1([F:30])[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@H:16]([C:26](OC)=[O:27])[CH2:15]1>C1COCC1>[F:30][C:14]1([F:13])[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[C@H:16]([C:26](=[O:27])[NH:7][C:2]2[CH:3]=[N:4][CH:5]=[CH:6][N:1]=2)[CH2:15]1

Participants

5

Reactant 3

HCID 78747AminopyrazineHCID 11129200N-Boc-4,4-difluoro-L-proline methyl esterHCID 178418918HCID 178418918, compound

Product 1

HCID 59436366HCID 59436366, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of pyrazin-2-amine (4.30 g, 45.2 mmol) in 50 mL of THF was added isopropylmagnesium chloride (16.96 mL, 33.9 mmol) dropwise under nitrogen atmosphere. A solid precipitated from the solution. After 15 min, a solution of (S)-1-tert-butyl 2-methyl 4,4-difluoropyrrolidine-1,2-dicarboxylate 116A (3 g, 11.31 mmol) in 50 mL of THF was added and stirred for 2 hr. The solvent was evaporated to dryness at the reduced pressure. The residue was suspended in ethyl acetate, washed with water, brined and dried. Evaporation of the solvent furnished a solid, which was chromatographed (20% ethyl acetate, CH2Cl2) to give 116B. LC/MS [M+H]+: 329; Ret time (Method F): 2.42 min.

Workup

  1. customA solid precipitated from the solution
  2. customThe solvent was evaporated to dryness at the reduced pressure
  3. washwashed with water
  4. customdried
  5. customEvaporation of the solvent
  6. customfurnished a solid, which
  7. customwas chromatographed (20% ethyl acetate, CH2Cl2)

Sources & evidence

ORD record
ord-ff52cd0d8c1b425caa8bc7bb0488b7c8
Source dataset
uspto-grants-2013_04
Patent number
US08415340B2

Reaction notes

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