Acetonitrile → HCID 57949324, compound

HRID 2427548Notes

Reaction equation

HRID 2427548 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.[CH3:10][C:11]1[CH:12]=[C:13]([CH2:33][CH:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)[CH:14]=[C:15]2[C:19]=1[C:18](=[O:20])[N:17]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=1)[CH2:16]2.C(=O)([O-])[O-].[K+].[K+].C(#N)C>O>[CH3:10][C:11]1[CH:12]=[C:13]([CH2:33][CH:34]2[CH2:35][CH2:36][N:37]([CH2:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=3)[CH2:38][CH2:39]2)[CH:14]=[C:15]2[C:19]=1[C:18](=[O:20])[N:17]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]([F:31])([F:32])[F:30])=[CH:24][CH:23]=1)[CH2:16]2

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 23392Picolyl chloride hydrochlorideHCID 57949296HCID 57949296, compound

Product 1

HCID 57949324HCID 57949324, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-chloromethylpyridine hydrochloride salt (16.9 mg, 0.103 mmol), 7-methyl-5-piperidin-4-ylmethyl-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (50.0 mg, 0.120 mmol) and potassium carbonate (71.2 mg, 0.515 mmol) was added acetonitrile (3.0 mL). The mixture was allowed to stir at room temperature overnight. Water (2.0 mL) was added and the product was extracted with ethyl acetate. The organic layer was washed with water, brine, dried over sodium sulfate, filtered and concentrated. Column chromatography provided the title compound as a yellow oil (34.1 mg, 65%). 1H NMR (300 MHz, CDCl3): δ 8.56 (d, 1H), 7.65 (t, 1H), 7.34 (m, 3H), 7.18 (m, 3H), 6.98 (d, 2H), 4.76 (s, 2H), 4.20 (s, 2H), 3.64 (s, 2H), 2.90 (d, 2H), 2.73 (s, 3H), 2.57 (d, 2H), 2.03 (t, 2H), 1.62 (m, 2H), 1.35 (m, 3H).

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8c9a343fd1bc4c059b53fa189d2def23
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

Loading…