HCID 57752702, compound → HCID 57752701, compound

HRID 226057Notes

Reaction equation

HRID 226057 reaction equation
[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[C:18]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([CH3:29])=[CH2:28])[C:19]=4[S:20][C:21]=3[CH3:22])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2]>CO.[Pd]>[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[C:18]4[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]([CH3:29])[CH3:28])[C:19]=4[S:20][C:21]=3[CH3:22])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 1

HCID 57752702HCID 57752702, compound

Product 1

HCID 57752701HCID 57752701, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 8-(1-ethyl-propyl)-3-(7-isopropenyl-2-methyl-benzo[b]thiophen-3-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (33 mg, 0.08 mmol) in CH3OH (25 mL) is hydrogenated at 30 psi/RT/1 h using 10% Pd—C (99 mg). The reaction mixture is filtered through celite, washed with EtOAc and concentrated to give the title compound (13.6 mg, 0.03 mmol, 41%). 1H NMR (CDCl3): δ 0.92 (t, J=7.5 Hz, 6H), 1.42 (d, J=2.6 Hz, 3H), 1.44 (d, J=2.6 Hz, 3H), 1.75-1.95 (m, 4H), 2.40 (s, 3H), 2.41 (s, 3H), 2.45 (s, 3H), 3.20-3.30 (m, 1H), 3.35-3.50 (m, 1H), 6.69 (s, 1H), 7.07 (d, J=7.5 Hz, 1H), 7.18 (d, J=7.0 Hz, 1H), 7.26 (t, J=7.9 Hz, 1H) ppm. ES-MS (m/z): calcd for C25H31N3S (M+H)+: 406.6. found: 406.3.

Workup

  1. customis hydrogenated at 30 psi/RT/1 h
  2. filtrationThe reaction mixture is filtered through celite
  3. washwashed with EtOAc
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7611ef369a7e4e94bd6301835eae34ad
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

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