Ammonia → HCID 135876020, compound

HRID 1893467Notes

Reaction equation

HRID 1893467 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[C:7]2[N:8]([C:20]([CH:23]=O)=[CH:21][N:22]=2)[C:9]2[C:14]([N:15]=1)=[CH:13][C:12]([C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=2.C(C=O)=O.N.[NH:30]1[CH:34]=[CH:33][N:32]=C1>CO>[NH:30]1[CH:34]=[CH:33][N:32]=[C:23]1[C:20]1[N:8]2[C:9]3[C:14]([N:15]=[C:6]([NH:5][CH2:4][CH2:3][CH2:2][OH:1])[C:7]2=[N:22][CH:21]=1)=[CH:13][C:12]([C:16]([F:18])([F:17])[F:19])=[CH:11][CH:10]=3

Participants

6

Reactant 4

HCID 222AmmoniaHCID 795ImidazoleHCID 7860GlyoxalHCID 25120537HCID 25120537, compound

Product 1

HCID 135876020HCID 135876020, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-[(3-hydroxypropyl)amino]-7-(trifluoromethyl)imidazo[1,2-a]quinoxalin-1-carbaldehyde (35 mg, 0.10 mmol) in methanol (1.2 mL) was added glyoxal (40% in water, 15 μL, 0.10 mmol). The mixture was cooled at 0° C. and NH3 (2M in ethanol, 150 μL, 0.30 mmol) was added. The reaction was stirred at 25° C. under argon overnight. The reaction was followed by TLC that showed small conversion of the starting material in imidazole. The addition of reactants was repeated 4 times in 4 days, until the TLC indicated completion of the reaction. The reaction was concentrated. The crude product was purified twice by preparative TLC (dichloromethane/methanol 9/1) to give the title compound (7 mg, 18%) as a beige powder.

Workup

  1. additionThe addition of reactants
  2. customin 4 days
  3. customcompletion of the reaction
  4. concentrationThe reaction was concentrated
  5. customThe crude product was purified twice by preparative TLC (dichloromethane/methanol 9/1)

Sources & evidence

ORD record
ord-ed62a32e955e4f8aa9a3815b08b3f273
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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