6-Aminonicotinamide → HCID 86762306, compound

HRID 1191708Notes

Reaction equation

HRID 1191708 reaction equation
COC(=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.NC1C=CC([C:38]([NH2:40])=[O:39])=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[S:13][CH2:12][C:11]([NH:10][C:7]2[N:6]=[CH:5][CH:4]=[CH:9][C:8]=2[C:38]([NH2:40])=[O:39])=[O:31])=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 95006-AminonicotinamideHCID 16058694HCID 16058694, compound

Product 1

HCID 86762306HCID 86762306, compound

Procedure

The product from Example 1, Part C (160 mg, 0.5 mmol) and 6-aminonicotinamide (103 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, and 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 (10 mg, 5%). 1H NMR (300 MHz, CDCl3) δ 8.76 (d, J=2 Hz, 1H), 8.71 (br s, 1H), 8.22 (d, J=9 Hz, 1H), 8.13 (dd, J=9 Hz, 2 Hz, 1H), 7.20 (d, J=9 Hz, 2H), 6.83 (d, J=9 Hz, 2H), 5.05 (d, J=15 Hz, 1H), 4.63 (s, 1H), 4.13 (d, J=15 Hz, 1H), 3.77 (s, 3H), 2.94 (s, 2H), 1.95 (s, 3H), 1.83 (s, 3H). MS: m/z (MH+) 441.

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-2ae3e4cf75804f0aa7f939363ffc2bae
Source dataset
uspto-grants-2014_03
Patent number
US08680122B2

Reaction notes

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