Stannane, tributyl(1-ethoxyethenyl)- → HCID 11342349, compound

HRID 1591723Notes

Reaction equation

HRID 1591723 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][CH:12]2[CH2:17][CH:16]([N:18]([CH:20]([CH3:22])[CH3:21])[CH3:19])[CH2:15][CH2:14][CH:13]2[NH:23][C:24](=[O:39])[CH2:25][C:26]2[NH:30][C:29]3[CH:31]=[CH:32][CH:33]=[C:34]([C:35]([F:38])([F:37])[F:36])[C:28]=3[N:27]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:40]([O:42]C([Sn](CCCC)(CCCC)CCCC)=C)[CH3:41]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:40]([C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C@@H:12]2[CH2:17][C@H:16]([N:18]([CH:20]([CH3:21])[CH3:22])[CH3:19])[CH2:15][CH2:14][C@@H:13]2[NH:23][C:24](=[O:39])[CH2:25][C:26]2[NH:30][C:29]3[CH:31]=[CH:32][CH:33]=[C:34]([C:35]([F:36])([F:37])[F:38])[C:28]=3[N:27]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1)(=[O:42])[CH3:41]

Participants

5

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 68637241HCID 68637241, compound

Product 1

HCID 11342349HCID 11342349, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

(1S,2R,4R)—(N-[2-(4-Bromo-benzenesulfonylmethyl)-4-(isopropyl-methyl-amino)-cyclohexyl]-2-(4-trifluoromethyl-1H-benzoimidazol-2-yl)-acetamide, Example 3, (50 mg) was dissolved in toluene (1 ml) prior to the addition of 1-ethoxyvinyltri-n-butyltin (0.5 ml), Pd(PPh3)4 (20 mg) and a few crystals of 2,6-tert-butyl-4-methyl phenol. The resulting solution was heated to reflux overnight. After cooling, the palladium catalyst was filtered off and the solution was concentrated. The residue was dissolved in dioxane (1 ml) prior to the addition of 1N HCl. The resulting solution was stirred at rt for 2 h. The solution was concentrated. Reverse phase HPLC purification (gradient elution, water/acetonitrile/TFA) of the resulting residue provided the title compound (8 mg). MS found: (M+H)+=593.5.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux overnight
  3. temperatureAfter cooling
  4. filtrationthe palladium catalyst was filtered off
  5. concentrationthe solution was concentrated
  6. dissolutionThe residue was dissolved in dioxane (1 ml)
  7. additionto the addition of 1N HCl
  8. concentrationThe solution was concentrated
  9. customReverse phase HPLC purification (gradient elution, water/acetonitrile/TFA) of the resulting residue

Sources & evidence

ORD record
ord-5075c4c9244c43a8b5deff74dc3d52bb
Source dataset
uspto-grants-2007_11
Patent number
US07291615B2

Reaction notes

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