2-Aminopyridine → HCID 58869960, compound

HRID 1191714Notes

Reaction equation

HRID 1191714 reaction equation
COC(=O)[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:31])[CH2:12][O: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.NC1C=CC=CN=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[O:13][CH2:12][C:11]([NH:10][C:7]2[CH:8]=[CH:9][CH:4]=[CH:5][N:6]=2)=[O:31])=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 104392-AminopyridineHCID 67482186HCID 67482186, compound

Product 1

HCID 58869960HCID 58869960, compound

Procedure

The product from Example 27, Part B (90 mg, 0.3 mmol) and 2-aminopyridine (42 mg, 0.45 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 white solid by silica gel chromatography (40 mg, 35%). 1H NMR (300 MHz, CDCl3) δ 8.72 (br s, 1H), 8.33 (d, J=4 Hz, 1H), 8.18 (d, J=8 Hz, 1H), 7.72 (m, 1H), 7.23 (d, J=9 Hz, 2H), 7.08 (m, 1H), 6.79 (d, J=9 Hz, 2H), 5.17 (s, 1H), 4.73 (d, J=15 Hz, 1H), 4.23 (d, J=15 Hz, 1H), 3.70 (d, J=15 Hz, 1H), 3.69 (s, 3H), 3.59 (d, J=15 Hz, 1H), 1.87 (s, 6H). MS: m/z (MH+) 382.

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-9be3faf70d8546f195d53d1f64045fd7
Source dataset
uspto-grants-2014_03
Patent number
US08680122B2

Reaction notes

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