Aminopyrazine → HCID 58869952, compound

HRID 1191700Notes

Reaction equation

HRID 1191700 reaction equation
COC(=O)[C:4]1C=[CH:8][C:7]([NH:10][C:11](=[O:31])[CH2:12][S:13][CH:14]2[C:18]([CH3:19])=[C:17]([CH3:20])[C:16](=[O:21])[N:15]2[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)=[N:6][CH:5]=1.[NH2:33]C1C=NC=CN=1>>[CH3:30][O:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][N:15]2[C:16](=[O:21])[C:17]([CH3:20])=[C:18]([CH3:19])[CH:14]2[S:13][CH2:12][C:11]([NH:10][C:7]2[CH:8]=[N:33][CH:4]=[CH:5][N:6]=2)=[O:31])=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 78747AminopyrazineHCID 16058694HCID 16058694, compound

Product 1

HCID 58869952HCID 58869952, compound

Procedure

The product from Example 1, Part C (200 mg, 0.6 mmol) and 2-aminopyrazine (89 mg, 0.9 mmol) were reacted as described in Example 5. After evaporation of the reaction solvent the residue was partitioned between water and EtOAc, and the organic phase was washed with EtOAc. The combined organics were washed with brine, dried (Na2SO4), filtered, and evaporated. The title compound was obtained as a tan solid by silica gel chromatography. 1H NMR (400 MHz, CDCl3) δ 9.48 (s, 1H), 8.70 (br s, 1H), 8.36 (d, J=2 Hz, 1H), 8.20 (m, 1H), 7.22 (d, J=8 Hz, 2H), 6.83 (d, J=8 Hz, 2H), 5.14 (d, J=14 Hz, 1H), 4.63 (s, 1H), 4.16 (d, J=14 Hz, 1H), 3.77 (s, 3H), 3.04 (d, J=16 Hz, 1H), 2.97 (d, J=16 Hz, 1H), 1.95 (s, 3H), 1.84 (s, 3H). MS: m/z (MH+) 399.

Workup

  1. customAfter evaporation of the reaction solvent the residue
  2. customwas partitioned between water and EtOAc
  3. washthe organic phase was washed with EtOAc
  4. washThe combined organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-73da6d1ac1d94d868ea5b2e15e3b24a7
Source dataset
uspto-grants-2014_03
Patent number
US08680122B2

Reaction notes

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