2-Amino-5-chloropyridine → HCID 58869971, compound

HRID 1191702Notes

Reaction equation

HRID 1191702 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.[Cl:33]C1C=CC(N)=NC=1>>[Cl:33][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

Participants

3

Reactant 2

HCID 661742-Amino-5-chloropyridineHCID 16058694HCID 16058694, compound

Product 1

HCID 58869971HCID 58869971, compound

Procedure

The product from Example 1, Part C and 5-chloropyridin-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 (300 MHz, CDCl3) δ 8.47 (br s, 1H), 8.22 (d, J=2 Hz, 1H), 8.12 (d, J=9 Hz, 1H), 7.66 (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), 4.62 (s, 1H), 4.13 (d, J=15 Hz, 1H), 3.77 (s, 3H), 2.91 (s, 2H), 1.94 (s, 3H), 1.84 (s, 3H). MS: m/z (MH+) 432.

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-05b9baa61e9d40bfbcb08147b8cb9bb5
Source dataset
uspto-grants-2014_03
Patent number
US08680122B2

Reaction notes

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