Dichloromethane → HCID 57423902, compound

HRID 2064092Notes

Reaction equation

HRID 2064092 reaction equation
[O:1]=[C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][N:10]([C:13]3([C:19]#N)[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[CH2:9][CH2:8]2)[C:5]2[CH:21]=[C:22]([O:25][C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:24][C:4]=2[NH:3]1.C[Mg]Br.[Cl-].[NH4+].[Cl:35]CCl>O1CCCC1.O>[ClH:35].[CH3:19][C:13]1([N:10]2[CH2:9][CH2:8][CH:7]([N:6]3[C:5]4[CH:21]=[C:22]([O:25][C:26]([F:27])([F:29])[F:28])[CH:23]=[CH:24][C:4]=4[NH:3][C:2]3=[O:1])[CH2:12][CH2:11]2)[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 25517Ammonium ChlorideHCID 59863012HCID 59863012, compoundHCID 178418573HCID 178418573, compound2×

Product 1

HCID 57423902HCID 57423902, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

4-{4-[2-Oxo-6-(trifluoromethoxy)-2,3-dihydro-1H-benzimidazol-1-yl]piperidin-1-yl}tetrahydro-2H-pyran-4-carbonitrile (D36, 62 mg) in tetrahydrofuran (5 ml) was treated with 3M methylmagnesium bromide solution in tetrahydrofuran (0.3 ml) and stirred for 2 hours. A second aliquot of 3M methylmagnesium bromide solution in tetrahydrofuran (0.3 ml) was added and the solution was stirred for 2 hours, then treated with saturated ammonium chloride solution (3 ml). The mixture was treated with dichloromethane and water. The dichloromethane layer was separated, dried by passing through a 3 g hydromatrix cartridge and the solvent was removed. The residue was dissolved in methanol and treated with hydrogen chloride in ether to give a white solid which partitioned between dichloromethane and sodium bicarbonate solution. The dichloromethane layer was separated, dried by passing through a hydromatrix cartridge and the solvent was removed. The residue was treated with hydrogen chloride in ether to give the title compound as a white solid (28 mg). M+ 400.

Workup

  1. stirringthe solution was stirred for 2 hours
  2. customThe dichloromethane layer was separated
  3. customdried
  4. customthe solvent was removed
  5. dissolutionThe residue was dissolved in methanol
  6. additiontreated with hydrogen chloride in ether
  7. customto give a white solid which
  8. custompartitioned between dichloromethane and sodium bicarbonate solution
  9. customThe dichloromethane layer was separated
  10. customdried
  11. customthe solvent was removed
  12. additionThe residue was treated with hydrogen chloride in ether

Sources & evidence

ORD record
ord-9bf12bc56fb94d02a1fe1b1c8865bacd
Source dataset
uspto-grants-2012_10
Patent number
US08288413B2

Reaction notes

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