Hydrochloric Acid → HCID 59732477, compound

HRID 131518Notes

Reaction equation

HRID 131518 reaction equation
[CH:1]1([CH2:7][NH:8][C:9]2[C:14]([CH2:15][C:16]([OH:18])=[O:17])=[CH:13][C:12]([NH:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:11][N:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[CH3:27]O>CCOC(C)=O>[CH3:27][O:17][C:16](=[O:18])[CH2:15][C:14]1[C:9]([NH:8][CH2:7][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)=[N:10][CH:11]=[C:12]([NH:19][C:20](=[O:25])[C:21]([CH3:22])([CH3:24])[CH3:23])[CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 59732495HCID 59732495, compound

Product 1

HCID 59732477HCID 59732477, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product 2-[(cyclohexylmethyl)amino]-5-[(2,2-dimethyl-1-oxopropyl)amino]-3-pyridineacetic acid in dry MeOH (7.5 mL) was added 4N HCl solution (in dioxane, 2.5 mL) at 0° C. The reaction mixture was stirred overnight at r.t, and then condensed under vacuum, diluted with AcOEt (50 mL), washed with 1N NH4OH (100 mL), brine (50 mL), and dried over MgSO4. Removal of solvent afforded desired title product (325 mg, 90%). 1H-NMR (CDCl3): δ 0.98 (m, 2H), 1.19 (m, 3H), 1.24 (s, 9H), 1.58 (m, 1H), 1.67 (m, 3H), 1.76 (m, 2H), 3.20 (d, J=6.8 Hz, 2H), 3.39 (s, 2H), 3.63 (s, 3H), 4.98 (brs, 1H), 7.24 (brs, 1H), 7.680 (s, 1H), 7.92 (s, 1H).

Workup

  1. customcondensed under vacuum
  2. washwashed with 1N NH4OH (100 mL), brine (50 mL)
  3. dry with materialdried over MgSO4
  4. customRemoval of solvent

Sources & evidence

ORD record
ord-7be08d32f2d44d1d94c12a6d3deb6c8d
Source dataset
uspto-grants-2008_06
Patent number
US07384955B2

Reaction notes

Loading…