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Potassium Carbonate → HCID 53472322, compound

HRID 450503
Notes
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Reaction equation

HRID 450503 reaction equation
F[C:2]1[C:3](=[O:20])[N:4]([CH2:12][C:13]2[N:17]([CH3:18])[C:16](=[O:19])[NH:15][N:14]=2)[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].[F:21][CH:22]([F:32])[C:23]1[CH:24]=[C:25]([CH:28]=[C:29]([OH:31])[CH:30]=1)[C:26]#[N:27].C([O-])([O-])=O.[K+].[K+]>O>[F:21][CH:22]([F:32])[C:23]1[CH:24]=[C:25]([CH:28]=[C:29]([O:31][C:2]2[C:3](=[O:20])[N:4]([CH2:12][C:13]3[N:17]([CH3:18])[C:16](=[O:19])[NH:15][N:14]=3)[CH:5]=[CH:6][C:7]=2[C:8]([F:11])([F:10])[F:9])[CH:30]=1)[C:26]#[N:27]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 574435053-(Difluoromethyl)-5-hydroxybenzonitrileHCID 58460038HCID 58460038, compound

Product 1

HCID 53472322HCID 53472322, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 3-fluoro-1-[(4-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl]-4-(trifluoromethyl)pyridin-2(1 H)-one (8-8; 30 mg; 0.103 mmol), 3-(difluoromethyl)-5-hydroxybenzonitrile (8-7; 34.7 mg; 0.205 mmol) and K2CO3 (28.4 mg; 0.205 mmol) was heated to 75° C., and stirred overnight. After cooling to room temperature, the mixture was diluted with water and extracted with CH2Cl2. The combined organic extracts were dried (MgSO4) and concentrated in vacuo. Purification by mass-directed HPLC provided 2.1 mg (0.0048 mmol; 4.6%) of the title compound as a white solid. 1H NMR (400 MHz, DMSO): δ 11.70 (s, 1 H); 7.90 (d, J=7.3 Hz, 1 H); 7.80 (d, J=8.5 Hz, 2 H); 7.57 (s, 1 H); 7.05 (t, J=55.2 Hz, 1 H); 6.69 (d, J=7.3 Hz, 1 H); 5.17 (s, 2 H); 3.10 (s, 3 H).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by mass-directed HPLC

Sources & evidence

ORD record
ord-4336238dd9c143d4932c867626a9fbf6
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08486975B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes