Pyridine → HCID 69196950, compound

HRID 2376219Notes

Reaction equation

HRID 2376219 reaction equation
COC1[CH:8]=[CH:7][C:6]([N:9]2[C:13](C3C=CC(C)=CC=3)=[CH:12][C:11]([CH2:21][CH:22]([C:26]3[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=3)[C:23]([NH2:25])=O)=[N:10]2)=[CH:5][CH:4]=1.N1C=[CH:37][CH:36]=[CH:35][CH:34]=1.[C:39]([O:45][C:46]([C:48](F)(F)F)=O)(C(F)(F)F)=O.O1[CH2:57][CH2:56]OCC1>>[CH3:39][O:45][C:46]1[CH:48]=[CH:37][C:36]([C:56]2([CH3:57])[CH:4]=[CH:5][C:6]([N:9]3[CH:13]=[CH:12][C:11]([CH2:21][CH:22]([C:26]4[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=4)[C:23]#[N:25])=[N:10]3)=[CH:7][CH2:8]2)=[CH:35][CH:34]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 312751,4-DioxaneHCID 10455092HCID 10455092, compound

Product 1

HCID 69196950HCID 69196950, compoundYield 99%

Conditions

Temperature
0 °C

Procedure

To a solution of 3-[1-(4-methoxy-phenyl)-5-p-tolyl-1H-pyrazol-3-yl]-2-m-tolyl-propionamide (Example 65, 0.31 g, 0.73 mmol) in pyridine (0.115 mL, 1.46 mmol) and dioxane (2.0 mL) at 0° C. was added TFAA (0.11 mL, 0.80 mmol). The solution was stirred at 0° C. for 30 min, allowed to warm to rt and stirred for an additional 3 h. The solvent was removed under reduced pressure, and the residue was re-dissolved in EtOAc (100 mL). This solution was washed with water (1×50 mL) and brine (1×50 mL) and dried with Na2SO4, and then solvent was removed under reduced pressure giving 295 mg (>99%) of 3-[1-(4-methoxy-phenyl)-p-tolyl-1H-pyrazol-3-yl]-2-m-tolyl-propionitrile. HPLC: Rt=3.53 (Method B). MS (ES+): mass calculated for C27H25N3O, 407.20; m/z found 408.2 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 7.33-7.26 (m, 3H), 7.18-7.12 (m, 5H), 7.08 (d, J=8.2 Hz, 2H), 6.95 (d, J=8.9 Hz, 2H), 6.48 (s, 1H), 4.58 (dd, J=5.9, 9.6 Hz, 1H), 3.77 (s, 3H), 3.27 (dd, J=9.6, 14.6 Hz, 1H), 3.15 (dd, J=5.9, 14.6 Hz, 1H), 2.33 (s, 3H), 2.28 (s, 3H).

Workup

  1. temperatureto warm to rt
  2. stirringstirred for an additional 3 h
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was re-dissolved in EtOAc (100 mL)
  5. washThis solution was washed with water (1×50 mL) and brine (1×50 mL)
  6. dry with materialdried with Na2SO4
  7. customsolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9d423993826b4a01aea2f52bceac6ee1
Source dataset
uspto-grants-2008_12
Patent number
US07465808B2

Reaction notes

Loading…