Pyridine → HCID 59003233, compound

HRID 2353867Notes

Reaction equation

HRID 2353867 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH:6]([O:9][C:10]([N:12]1[CH2:18][CH2:17][CH2:16][CH:15]([N:19]([C:35](=[O:37])[CH3:36])[CH2:20][C:21]2[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:22]=2)[C:14]2[CH:38]=[C:39]([NH2:42])[CH:40]=[CH:41][C:13]1=2)=[O:11])([CH3:8])[CH3:7].N1C=CC=CC=1>ClCCl>[C:35]([N:19]([CH2:20][C:21]1[CH:22]=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:24]=[C:25]([C:27]([F:30])([F:28])[F:29])[CH:26]=1)[CH:15]1[CH2:16][CH2:17][CH2:18][N:12]([C:10]([O:9][CH:6]([CH3:8])[CH3:7])=[O:11])[C:13]2[CH:41]=[CH:40][C:39]([NH:42][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:38][C:14]1=2)(=[O:37])[CH3:36]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 59003169HCID 59003169, compound

Product 1

HCID 59003233HCID 59003233, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add methanesulfonyl chloride (8 μl, 0.103 mmol) dropwise to a suspension of isopropyl-5-[acetyl-(3,5-bistrifluoromethylbenzyl)amino]-7-amino-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate (0.050 g, 0.094 mmol) and pyridine (8 μl, 0.103 mmol) in dichloromethane (2 mL) at 0° C. under atmosphere of nitrogen. Stir the suspension for 30 min, then remove the cooling bath and warm to room temperature while stirring overnight. Dilute the mixture with dichloromethane (30 mL) and wash with 2 N hydrochloric acid, water, and brine (10 mL each). Dry the organic layer over anhydrous sodium sulfate, filter and remove the solvent under reduced pressure. Chromatograph the residue over silica gel, eluting with ethyl acetate/hexanes (10:1 to 1:2), to provide the title compound as a white solid (0.037 g, 65%): ESI MS 610 (M+H).

Workup

  1. customremove the cooling bath
  2. stirringwhile stirring overnight
  3. additionDilute the mixture with dichloromethane (30 mL)
  4. washwash with 2 N hydrochloric acid, water, and brine (10 mL each)
  5. dry with materialDry the organic layer over anhydrous sodium sulfate
  6. filtrationfilter
  7. customremove the solvent under reduced pressure
  8. washChromatograph the residue over silica gel, eluting with ethyl acetate/hexanes (10:1 to 1:2)

Sources & evidence

ORD record
ord-31bd0702d793470dac7cfbebf6d067e8
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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