Pyridine → HCID 59003141, compound

HRID 2353984Notes

Reaction equation

HRID 2353984 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:6][NH:7][CH:8]1[CH2:14][CH2:13][CH2:12][N:11]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:10]2[CH:25]=[CH:26][CH:27]=[CH:28][C:9]1=2.N1C=CC=CC=1.[C:44](OC(=O)C)(=[O:46])[CH3:45].[OH-].[Na+]>ClCCl.Cl>[F:37][C:2]([F:1])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:33])([F:34])[F:35])[CH:31]=1)[CH2:6][N:7]([CH:8]1[CH2:14][CH2:13][CH2:12][N:11]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:16])=[O:17])[C:10]2[CH:25]=[CH:26][CH:27]=[CH:28][C:9]1=2)[C:44](=[O:46])[CH3:45]

Participants

7

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 86616086HCID 86616086, compound

Product 1

HCID 59003141HCID 59003141, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (+/−) (3,5-Bis-trifluoromethyl-benzyl)-[1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl]-amine (149 mg, 0.27 mmol) and pyridine (0.33 ml, 4 mmol) in dichloromethane (1.5 ml) at room temperature is added acetic anhydride (0.38 ml, 4.1 mmol) via dropwise addition over 2 minutes. The mixture is stirred at room temperature for 20 hours. The mixture is treated with 1N aqueous NaOH (4 ml) and stirred for 10 minutes, then diluted with 1N HCl (15 ml) and dichloromethane (15 ml). The organic layer is washed with water, dried (Na2SO4), and concentrated to a solid. Purification by silica gel column chromatography (eluent, 35% ethyl acetate in hexanes) gives the title compound as a solid. Mass spectrum (ES+): 585 (M+H).

Workup

  1. additionvia dropwise addition over 2 minutes
  2. stirringstirred for 10 minutes
  3. washThe organic layer is washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated to a solid
  6. customPurification by silica gel column chromatography (eluent, 35% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-f990d746bc08468da7c251c7c3ae7836
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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