2-Amino-5-cyanopyridine → HCID 67482521, compound

HRID 1191707Notes

Reaction equation

HRID 1191707 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.[NH2:33]C1C=CC(C#N)=CN=1>>[C:3]([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)#[N:33]

Participants

3

Reactant 2

HCID 8182602-Amino-5-cyanopyridineHCID 16058694HCID 16058694, compound

Product 1

HCID 67482521HCID 67482521, compound

Procedure

The product from Example 1, Part C (160 mg, 0.5 mmol) and 6-aminonicotinonitrile (89 mg, 0.75 mmol) were reacted as described in Example 5. After evaporation of the reaction solvent the residue was partitioned between water and EtOAc, the aqueous 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 (30 mg, 14%). 1H NMR (400 MHz, CDCl3) δ 8.84 (br s, 1H), 8.55 (d, J=2 Hz, 1H), 8.30 (d, J=9 Hz, 1H), 7.95 (dd, J=9 Hz, 2 Hz, 1H), 7.21 (d, J=9 Hz, 2H), 6.83 (d, J=9 Hz, 2H), 5.07 (d, J=15 Hz, 1H), 4.63 (s, 1H), 4.12 (d, J=15 Hz, 1H), 3.77 (s, 3H), 2.96 (m, 2H), 1.94 (s, 3H), 1.84 (s, 3H). MS: m/z (MNa+) 445.

Workup

  1. customAfter evaporation of the reaction solvent the residue
  2. customwas partitioned between water and EtOAc
  3. washthe aqueous 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-e873621aaf5244fcad392202f06798e6
Source dataset
uspto-grants-2014_03
Patent number
US08680122B2

Reaction notes

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