Benzaldehyde → HCID 11667000, compound

HRID 1991467Notes

Reaction equation

HRID 1991467 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([CH3:13])=[CH:8][C:9]=2[CH2:11][OH:12])[S:4][C:3]=1[C:14]([NH2:16])=[O:15].[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O.C(OCC)(=O)C>C(O)(=O)C>[OH:12][CH2:11][C:9]1[C:10]2[C:2]3[NH:1][CH:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[NH:16][C:14](=[O:15])[C:3]=3[S:4][C:5]=2[N:6]=[C:7]([CH3:13])[CH:8]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 962WaterHCID 8857Ethyl AcetateHCID 11579568HCID 11579568, compound

Product 1

HCID 11667000HCID 11667000, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3-amino-4-hydroxymethyl-6-methyl-thieno[2,3-b]pyridine-2-carboxamide (100 mg, 0.42 mmol) in acetic acid (2 mL) was added benzaldehyde (53 mg, 0.50 mmol) and the mixture was heated to reflux for 16 h. After cooling to room temperature, water (2 mL) and ethyl acetate (2 mL) were added to it. The reaction was further extracted with ethyl acetate (2 mL×3). The combined organic layers were washed with brine, dried over Na2SO4 and evaporated under reduced pressure. The residue was purified by preparative HPLC to give the title compound, 4-hydroxymethyl-2-methyl-6-phenyl-6,7-dihydro-5H-9-thia-1,5,7-triaza-fluoren-8-one (16 mg, 12%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 16 h
  3. extractionThe reaction was further extracted with ethyl acetate (2 mL×3)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated under reduced pressure
  7. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-d8727840c9b54a9985aa6e0aee34f620
Source dataset
uspto-grants-2010_01
Patent number
US07645881B2

Reaction notes

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