HCID 11192943, compound → HCID 11342351, compound

HRID 641580Notes

Reaction equation

HRID 641580 reaction equation
Br[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]([CH3:22])[CH3:21])[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:38])([F:37])[F:36])[C:28]=3[N:27]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Br-].[CH2:41]([Zn+])[CH2:42][CH3:43]>C1COCC1.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>[CH:20]([N:18]([CH3:19])[C@@H:16]1[CH2:15][CH2:14][C@H:13]([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)[C@H:12]([CH2:11][S:8]([C:5]2[CH:6]=[CH:7][C:2]([CH2:41][CH2:42][CH3:43])=[CH:3][CH:4]=2)(=[O:10])=[O:9])[CH2:17]1)([CH3:22])[CH3:21]

Participants

5

Reactant 2

HCID 11192943HCID 11192943, compoundHCID 178455869HCID 178455869, compound

Product 1

HCID 11342351HCID 11342351, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
150 °C

Procedure

(1S,2R,4R)-N-[2-(4-Bromo-benzenesulfonylmethyl)-4-(isopropyl-methyl-amino)-cyclohexyl]-2-(4-trifluoromethyl-1H-benzoimidazol-2-yl)-acetamide, Example 3, was dissolved in THF (1 ml) prior to the addition of propyl zinc bromide (0.32 ml), Pd(PPh3)4 (3 mg). The mixture was stirred under microwave conditions (150° C.) for 5 min. After cooling, the crude reaction was filtered and the filtrate was concentrated. Reverse phase HPLC purification (gradient elution, water/acetonitrile/TFA) of the resulting residue provided the two fractions, one of which contained the title compound (8 mg). MS found: (M+H)+=594.5

Workup

  1. temperatureAfter cooling
  2. customthe crude reaction
  3. filtrationwas filtered
  4. concentrationthe filtrate was concentrated
  5. customReverse phase HPLC purification (gradient elution, water/acetonitrile/TFA) of the resulting residue
  6. customprovided the two fractions, one of which

Sources & evidence

ORD record
ord-40ff239fb07c46f0896edce52d913259
Source dataset
uspto-grants-2010_04
Patent number
US07696205B2

Reaction notes

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