HCID 10027123, compound → HCID 11740079, compound

HRID 751306Notes

Reaction equation

HRID 751306 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:16]3[CH:17]=[CH:18][C:19]4[N:23]=[CH:22][N:21]([CH2:24][CH2:25][CH2:26][O:27]C5CCCCO5)[C:20]=4[CH:34]=3)=[C:10]3[CH2:15][CH2:14][CH2:13][N:11]3[N:12]=2)[CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.O1CCCC1.O>[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:16]3[CH:17]=[CH:18][C:19]4[N:23]=[CH:22][N:21]([CH2:24][CH2:25][CH2:26][OH:27])[C:20]=4[CH:34]=3)=[C:10]3[CH2:15][CH2:14][CH2:13][N:11]3[N:12]=2)[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 10027123HCID 10027123, compound

Product 1

HCID 11740079HCID 11740079, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

Heat a solution of (6-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-1-[3-(tetrahydro-pyran-2-yloxy)-propyl]-1H-benzoimidazole (Example 54; 368 mg mg, 0.8 mmol) in 4:2:1 acetic acid/tetrahydrofuran/water (20 mL) to 80° C. for 18 h. Remove the solvent in vacuo and dissolve the residue in excess 3:1 chloroform/isopropyl alcohol. Wash the organic layer with saturated sodium bicarbonate, dry over sodium sulfate, filter, and concentrate in vacuo. Purify the residue by column chromatography on silica gel eluting with dichloromethane to 10% methanol/90% dichloromethane to give the desired product as a white solid (225 mg, 75%). MS ES+ m/e 374.3 (M+1).

Workup

  1. customRemove the solvent in vacuo
  2. dissolutiondissolve the residue in excess 3:1 chloroform/isopropyl alcohol
  3. washWash the organic layer with saturated sodium bicarbonate
  4. dry with materialdry over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customPurify the residue by column chromatography on silica gel eluting with dichloromethane to 10% methanol/90% dichloromethane

Sources & evidence

ORD record
ord-8de8c38f1210417a92816578024f8007
Source dataset
uspto-grants-2008_07
Patent number
US07405299B2

Reaction notes

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