Ammonium Acetate → 2-[5-methyl-1-(tetrahydro-2H-pyran-2-yl)-3-(trifluoromethyl)-1H-pyrazol-4-yl]imidazo[4,5-d]dipyrido[2,3-b:4',3'-f]azepin-3(8H)-ol

HRID 75214Notes

Reaction equation

HRID 75214 reaction equation
[N:1]1[C:6]2[NH:7][C:8]3[CH:18]=[N:17][CH:16]=[CH:15][C:9]=3/[C:10](=[N:13]/[OH:14])/[C:11](=O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C([O-])(=O)C.[NH4+:23].[CH3:24][C:25]1[N:29]([CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][O:31]2)[N:28]=[C:27]([C:36]([F:39])([F:38])[F:37])[C:26]=1[CH:40]=O>C(O)(=O)C>[CH3:24][C:25]1[N:29]([CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][O:31]2)[N:28]=[C:27]([C:36]([F:39])([F:38])[F:37])[C:26]=1[C:40]1[N:13]([OH:14])[C:10]2[C:9]3[CH:15]=[CH:16][N:17]=[CH:18][C:8]=3[NH:7][C:6]3[N:1]=[CH:2][CH:3]=[CH:4][C:5]=3[C:11]=2[N:23]=1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 866132695-methyl-1-(tetrahydro-2H-pyran-2-yl)-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehydeHCID 178516816HCID 178516816, compound

Product 1

HCID 689792362-[5-methyl-1-(tetrahydro-2H-pyran-2-yl)-3-(trifluoromethyl)-1H-pyrazol-4-yl]imidazo[4,5-d]dipyrido[2,3-b:4',3'-f]azepin-3(8H)-ol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (6Z)-5H-dipyrido[2,3-b:4′,3′-f]azepine-5,6(11H)-dione 6-oxime (930 mg, 3.9 mmol), ammonium acetate (5.58 g, 72.4 mmol) and 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehyde (2.03 g, 7.74 mmol) in acetic acid (5.6 mL) was stirred at 80° C. for 2 h. The reaction was cooled to ambient temperature and partitioned between water and 3:1 CHCl3:isopropanol. The phases were separated and the aqueous phase was washed with additional solvent. The combined organic phase was washed with water, sat'd NaHCO3, then sat'd NaCl, dried over MgSO4 and reduced to dryness in vacuo to leave 2-[5-methyl-1-(tetrahydro-2H-pyran-2-yl)-3-(trifluoromethyl)-1H-pyrazol-4-yl]imidazo[4,5-d]dipyrido[2,3-b:4′,3′-f]azepin-3(8H)-ol, which was used without further purification. MS (EI) m/z=484.2 (M+H).

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. custompartitioned between water and 3:1 CHCl3
  3. customThe phases were separated
  4. washthe aqueous phase was washed with additional solvent
  5. washThe combined organic phase was washed with water
  6. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-4bba13ca1e504b7da691b66dc26ee91f
Source dataset
uspto-grants-2014_09
Patent number
US08835423B2

Reaction notes

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