Triethylamine → 1-(3-Tert-butyl-1-(3-fluorophenyl)-1H-pyrazol-5-yl)-3-(2-fluoro-4-(1-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yloxy)phenyl)urea

HRID 2409259Notes

Reaction equation

HRID 2409259 reaction equation
[C:1]([C:5]1[CH:9]=[C:8](C(O)=O)[N:7]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C([N:22]([CH2:25]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:34])C=CC=CC=1.[NH2:44][C:45]1[CH:62]=[CH:61][C:48]([O:49][C:50]2[CH:55]=[CH:54][N:53]=[C:52]3[NH:56][C:57](=[O:60])[N:58]([CH3:59])[C:51]=23)=[CH:47][C:46]=1[F:63]>CN(C=O)C.CCOC(C)=O>[C:1]([C:5]1[CH:9]=[C:8]([NH:22][C:25]([NH:44][C:45]2[CH:62]=[CH:61][C:48]([O:49][C:50]3[CH:55]=[CH:54][N:53]=[C:52]4[NH:56][C:57](=[O:60])[N:58]([CH3:59])[C:51]=34)=[CH:47][C:46]=2[F:63])=[O:34])[N:7]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)[N:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 441849547-(4-Amino-3-fluorophenoxy)-1-N-methyl-1H-imidazo[4,5-b]pyridin-2(3H)-oneHCID 57507619HCID 57507619, compound

Product 1

HCID 533392311-(3-Tert-butyl-1-(3-fluorophenyl)-1H-pyrazol-5-yl)-3-(2-fluoro-4-(1-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yloxy)phenyl)urea

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

3-Tert-butyl-1-(3-fluorophenyl)-1H-pyrazole-5-carboxylic acid (393 mg, 1.5 mmol) was dissolved in dry DMF (8 mL), and triethylamine (209 μL, 1.5 mmol) was added. The solution was cooled at 0° C., and diphenylphosphoryl azide (323 μL, 1.5 mmol) was added. The reaction mixture was stirred for 30 minutes at 0° C., followed by 1 hour at room temperature. 7-(4-Amino-3-fluorophenoxy)-1-N-thyl-1H-imidazo[4,5-b]pyridin-2(3H)-one (8a) (140 mg, 0.5 mmol) was added, and the reaction mixture heated at 110° C. for 1 hour. The solution was cooled, diluted with AcOEt (100 mL) and extracted with water and brine. The organic layer was dried and evaporated, and the residue taken up in DCM. The remaining solid was recovered by filtration to afford the title compound.

Workup

  1. waitfollowed by 1 hour at room temperature
  2. temperaturethe reaction mixture heated at 110° C. for 1 hour
  3. temperatureThe solution was cooled
  4. extractionextracted with water and brine
  5. customThe organic layer was dried
  6. customevaporated
  7. filtrationThe remaining solid was recovered by filtration

Sources & evidence

ORD record
ord-09f5c82dbac34efa934e06967cf84448
Source dataset
uspto-grants-2014_08
Patent number
US08815896B2

Reaction notes

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