Pyridine → (5-Benzenesulfonyl-1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester

HRID 2223245Notes

Reaction equation

HRID 2223245 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][CH:8]1[C:14](=[O:15])[N:13]([CH3:16])[C:12]2[CH:17]=[CH:18][CH:19]=[CH:20][C:11]=2[NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[C:22]1([S:28](Cl)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.N1C=CC=CC=1>ClCCl>[C:1]([O:5][C:6](=[O:21])[NH:7][CH:8]1[C:14](=[O:15])[N:13]([CH3:16])[C:12]2[CH:17]=[CH:18][CH:19]=[CH:20][C:11]=2[N:10]([S:28]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:30])=[O:29])[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 69038045HCID 69038045, compound

Product 1

HCID 69280061(5-Benzenesulfonyl-1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl esterYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.087 g (1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester in 1 ml of dichloromethane, 0.064 g of benzene sulfonyl chloride and 0.052 g of pyridine were added. The reaction mixture was stirred at room temperature for 16 hours. The reaction was quenched by addition of 1 M HCl (1 ml) and extracted with dichloromethane. The organic layer was washed with saturated NaHCO3, dried (MgSO4) and evaporated on the rotary evaporator to yield 0.113 g (95%) of the product as a light yellow foam.

Workup

  1. customThe reaction was quenched by addition of 1 M HCl (1 ml)
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with saturated NaHCO3
  4. dry with materialdried (MgSO4)
  5. customevaporated on the rotary evaporator

Sources & evidence

ORD record
ord-4f71893ffc4e46a9b752612b58a526e6
Source dataset
uspto-grants-2008_05
Patent number
US07375099B2

Reaction notes

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