4,6-Diamino-2-ethoxypyridine-3-carbonitrile → HCID 58504290, compound

HRID 2407674Notes

Reaction equation

HRID 2407674 reaction equation
Cl.[C:2]1([C:8]2[CH:12]=[C:11]([CH2:13][N:14]3[CH2:19][CH2:18][CH:17]([CH2:20][C:21](Cl)=[O:22])[CH2:16][CH2:15]3)[O:10][N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:24][C:25]1[C:30]([C:31]#[N:32])=[C:29]([O:33][CH2:34][CH3:35])[N:28]=[C:27]([NH2:36])[CH:26]=1>N1C=CC=CC=1.C(OCC)(=O)C>[NH2:24][C:25]1[C:30]([C:31]#[N:32])=[C:29]([O:33][CH2:34][CH3:35])[N:28]=[C:27]([NH:36][C:21](=[O:22])[CH2:20][CH:17]2[CH2:18][CH2:19][N:14]([CH2:13][C:11]3[O:10][N:9]=[C:8]([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH:12]=3)[CH2:15][CH2:16]2)[CH:26]=1

Participants

5

Reactant 2

HCID 131498684,6-Diamino-2-ethoxypyridine-3-carbonitrileHCID 86659054HCID 86659054, compound

Product 1

HCID 58504290HCID 58504290, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the compound prepared in Example 59 (100 mg) and 4,6-diamino-2-ethoxynicotinonitrile (50 mg, prepared according to the preparation reported in Szczepankiewicz, B. G.; et al. J. Med. Chem. 2006, 49, 3563 and references therein) in pyridine (1.5 mL) was heated to 50° C. overnight and then 80° C. for six days. The mixture was cooled to room temperature, diluted with ethyl acetate and washed twice with a saturated aqueous sodium bicarbonate solution. The organic phase was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=4:1) to obtain the title compound (18 mg) having the following physical data.

Workup

  1. customprepared
  2. washwashed twice with a saturated aqueous sodium bicarbonate solution
  3. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=4:1)

Sources & evidence

ORD record
ord-a32273a87df34fba9078fcc4368e0178
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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