Water → HCID 49783914, compound

HRID 1097214Notes

Reaction equation

HRID 1097214 reaction equation
[OH-].[NH4+:2].[CH3:3][N:4]([N:6]=[N:7][C:8]1[C:16]2[C:11](=[N:12][CH:13]=[CH:14][CH:15]=2)[Se:10][C:9]=1[C:17]([O:19]CC)=O)[CH3:5].O>C1COCC1>[CH3:3][N:4]([N:6]=[N:7][C:8]1[C:16]2[C:11](=[N:12][CH:13]=[CH:14][CH:15]=2)[Se:10][C:9]=1[C:17]([NH2:2])=[O:19])[CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 14923Ammonium HydroxideHCID 59547217HCID 59547217, compound

Product 1

HCID 49783914HCID 49783914, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice cold (0-5° C.) solution of ammonium hydroxide (15 mL) was added a solution of ethyl 3-[(dimethylamino)diazenyl]selenopheno[2,3-b]pyridine-2-carboxylate (150 mg) in THF (5 mL) for 5 min and stirred at rt for 16 h. The solution was poured into ice cooled water and extracted with ethyl acetate (3×100 mL). The combined EtOAc layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent. The residue was chromatographed over silica gel column using chloroform-methanol (95:5) as eluents to give the product as a light green color solid, which was recrystallized from chloroform-methanol-hexane (25 mg, 20%), mp 230-232° C. IR (Neat) νmax 3327, 3152, 2913, 1701, 1634, 1360, 1330, 1104, 1058, 1016, 878, 802 cm−1; 1H NMR (400 MHz, DMSO-d6): δ 8.80 (1H, d, J=8.4 Hz, H-4), 8.59 (1H, d, J=3.2 Hz, H-6), 8.18 (1H, s, —CONH2), 7.99 (1H, s, —CONH2), 7.46 (1H, dd, J=8.2, 4.6 Hz, H-5), 3.66 (3H, s, —NCH3), 3.26 (3H, s, —NCH3); 13C NMR (100 MHz, DMSO-d6): δ 164.4, 161.1, 148.3, 142.5, 136.2, 131.5, 130.4, 120.6, 43.6, 36.5; LC-MS (positive ion mode): m/z 318, 320 (M+Na)+.

Workup

  1. additionThe solution was poured into ice
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. washThe combined EtOAc layer was washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationThe solution was filtered
  6. customevaporated the solvent
  7. customThe residue was chromatographed over silica gel column
  8. customto give the product as a light green color solid, which
  9. customwas recrystallized from chloroform-methanol-hexane (25 mg, 20%), mp 230-232° C

Sources & evidence

ORD record
ord-93d8e192d4ec4f8c80e12977baf3feab
Source dataset
uspto-grants-2012_03
Patent number
US08143237B2

Reaction notes

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