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

HRID 1043471Notes

Reaction equation

HRID 1043471 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].[F:24][CH:25]([F:40])[C:26]1[C:30]([CH:31]=O)=[C:29]([CH3:33])[N:28]([CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][O:35]2)[N:27]=1.C(O)(=O)C>>[F:24][CH:25]([F:40])[C:26]1[C:30]([C:31]2[N:13]([OH:14])[C:10]3[C:9]4[CH:15]=[CH:16][N:17]=[CH:18][C:8]=4[NH:7][C:6]4[N:1]=[CH:2][CH:3]=[CH:4][C:5]=4[C:11]=3[N:23]=2)=[C:29]([CH3:33])[N:28]([CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][O:35]2)[N:27]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 517165Ammonium AcetateHCID 866132733-(difluoromethyl)-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-4-carbaldehydeHCID 178516816HCID 178516816, compound

Product 1

HCID 668871612-[3-(difluoromethyl)-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl]imidazo[4,5-d]dipyrido[2,3-b: 4',3'-f]azepin-3(8H)-ol

Conditions

Temperature
80 °C

Procedure

A mixture of (6Z)-5H-dipyrido[2,3-b:4′,3′-f]azepine-5,6(11H)-dione 6-oxime (1.00 g, 4.16 mmol), ammonium acetate (6.00 g, 77.8 mmol) and 3-(difluoromethyl)-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-4-carbaldehyde (2.50 g, 8.19 mmol) in acetic acid (6.0 mL, 0.106 mol) was stirred at 80° C. for 2 h. The reaction was partitioned between dichloromethane/isopropanol (5:1) and water and the organic extract was washed with NaHCO3, brine, dried (MgSO4) and concentrated in vacuo. The residue was used in the next reaction without purification. Mass spec: (EI) m/z=466 (M+1).

Workup

  1. customThe reaction was partitioned between dichloromethane/isopropanol (5:1) and water
  2. extractionthe organic extract
  3. washwas washed with NaHCO3, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was used in the next reaction without purification

Sources & evidence

ORD record
ord-2b6286f40feb43ab9bb268d40ef23dc3
Source dataset
uspto-grants-2013_10
Patent number
US08563541B2

Reaction notes

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