8-Amino-2-iodo-1-methyl-4,5-dihydro-1H-1,7,9-triaza-cyclopenta[a]naphthalene-3-carboxylic acid ethyl ester → HCID 68707164, compound

HRID 222133Notes

Reaction equation

HRID 222133 reaction equation
C([O:3][C:4]([C:6]1[C:10]2[CH2:11][CH2:12][C:13]3[C:18]([C:9]=2[N:8]([CH3:20])[C:7]=1[I:21])=[N:17][C:16]([NH2:19])=[N:15][CH:14]=3)=[O:5])C>CCO>[NH2:19][C:16]1[N:17]=[C:18]2[C:13]([CH2:12][CH2:11][C:10]3[C:6]([C:4]([OH:5])=[O:3])=[C:7]([I:21])[N:8]([CH3:20])[C:9]=32)=[CH:14][N:15]=1

Participants

3

Reactant 1

HCID 687058158-Amino-2-iodo-1-methyl-4,5-dihydro-1H-1,7,9-triaza-cyclopenta[a]naphthalene-3-carboxylic acid ethyl ester

Product 1

HCID 68707164HCID 68707164, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 8-amino-2-iodo-1-methyl-4,5-dihydro-1H-1,7,9-triaza-cyclopenta[a]naphthalene-3-carboxylic acid ethyl ester N1 (1.28 mmol) in 95% EtOH (30 mL) 4M NaOH (1.2 mL) was added. The mixture was heated to reflux for 10 h then cooled and evaporated to dryness. The residue was dissolved in 30 mL of water, acidified with glacial AcOH and the precipitate was filtered and washed with water. The product was dried affording the title compound (95% yield). ESI (+) MS: m/z 371 (MH+). 1H NMR: 2.63 (t, J=7.80, 2H), 2.90 (t, J=7.80, 2H), 4.18 (s, 3H), 6.33 (bs, 2H), 8.00 (s, 1H), 12.26 (bs, 1H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 10 h
  3. temperaturethen cooled
  4. customevaporated to dryness
  5. dissolutionThe residue was dissolved in 30 mL of water
  6. filtrationthe precipitate was filtered
  7. washwashed with water
  8. customThe product was dried

Sources & evidence

ORD record
ord-d25258c3712e4ea9b2dcfa8d4501930c
Source dataset
uspto-grants-2012_06
Patent number
US08207180B2

Reaction notes

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