Ethyl Acetate → HCID 136253018, compound

HRID 1027159Notes

Reaction equation

HRID 1027159 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[C:16]1[N:21]=[N:20][C:19]([N:22]([CH3:33])[CH:23]2[CH2:28][C:27]([CH3:30])([CH3:29])[NH:26][C:25]([CH3:32])([CH3:31])[CH2:24]2)=[CH:18][CH:17]=1)C1C=CC=CC=1.CCOC(C)=O>CO.C(Cl)Cl.[Pd]>[F:15][C:13]1[CH:12]=[CH:11][C:10]([C:16]2[N:21]=[N:20][C:19]([N:22]([CH3:33])[CH:23]3[CH2:28][C:27]([CH3:29])([CH3:30])[NH:26][C:25]([CH3:32])([CH3:31])[CH2:24]3)=[CH:18][CH:17]=2)=[C:9]([OH:8])[CH:14]=1

Participants

6

Reactant 2

HCID 8857Ethyl AcetateHCID 86710552HCID 86710552, compound

Product 1

HCID 136253018HCID 136253018, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Following GENERAL METHOD 4-1, Pd/C (10% wt, 47.0 mg, 0.044 mmol) was added to a solution of 6-(2-(benzyloxy)-4-fluorophenyl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine (198 mg, 0.441 mmol) in MeOH (2 mL)/EtOAc (2 mL) at RT. The reaction mixture was evacuated and filled with H2 (2×), then stirred under H2 atmosphere for 4 h and filtered through celite using MeOH. The filtrate was concentrated in vacuo affording a yellow oil, which was redissolved in DCM and concentrated in vacuo affording the title compound as a yellow solid (129 mg, 82% yield). LCMS Rt=0.49 min (LCMS method Q); MS (M+1)=359.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 14.10 (br. s, 1H), 8.11 (d, J=9.60 Hz, 1H), 7.83-7.92 (m, 1H), 7.32 (d, J=10.11 Hz, 1H), 6.67-6.77 (m, 2H), 4.83-4.98 (m, 1H), 2.95 (s, 3H), 1.54 (dd, J=12.13, 3.54 Hz, 2H), 1.43 (t, J=12.13 Hz, 2H), 1.25 (s, 6H), 1.09 (s, 6H).

Workup

  1. customThe reaction mixture was evacuated
  2. additionfilled with H2 (2×)
  3. filtrationfiltered through celite
  4. concentrationThe filtrate was concentrated in vacuo
  5. customaffording a yellow oil, which
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9d23229ea52a4e56a232a73380c34c10
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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