2-Amino-5-methylpyridine → HCID 58869965, compound

HRID 1191703Notes

Reaction equation

HRID 1191703 reaction equation
CO[C:3](=O)[C:4]1[CH:9]=[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.CC1C=CC(N)=NC=1>>[CH3:30][O:29][C:26]1[CH:25]=[CH:24][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]=[CH:9][C:4]([CH3:3])=[CH:5][N:6]=2)=[O:31])=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 153482-Amino-5-methylpyridineHCID 16058694HCID 16058694, compound

Product 1

HCID 58869965HCID 58869965, compound

Procedure

The product from Example 1, Part C and 5-methylpyridin-2-ylamine 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 by silica gel chromatography. 1H NMR (400 MHz, CDCl3) δ 8.43 (br s, 1H), 8.09 (m, 1H), 8.02 (d, J=9 Hz, 1H), 7.51 (m, 1H), 7.21 (d, J=9 Hz, 2H), 6.83 (d, J=9 Hz, 2H), 5.07 (d, J=15 Hz, 1H), 4.61 (s, 1H), 4.14 (d, J=15 Hz, 1H), 3.77 (s, 3H), 2.89 (m, 2H), 2.30 (s, 3H), 1.95 (s, 3H), 1.83 (s, 3H). MS: m/z (MH+) 412.

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-cb26f2c4857248469426ca57bdf08d84
Source dataset
uspto-grants-2014_03
Patent number
US08680122B2

Reaction notes

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