Pyridine → HCID 86592602, compound

HRID 413872Notes

Reaction equation

HRID 413872 reaction equation
[NH2:1][C@H:2]([C:4]([N:6]1[C:12](=[O:13])[CH:11]([CH3:14])[C:10]2[CH:15]=[CH:16][CH:17]=[CH:18][C:9]=2[C:8]2[C:19]([NH2:23])=[CH:20][CH:21]=[CH:22][C:7]1=2)=[O:5])[CH3:3].N1C=CC=CC=1.[CH2:30]([S:34](Cl)(=[O:36])=[O:35])[CH2:31][CH2:32][CH3:33]>CN(C=O)C>[CH2:30]([S:34]([NH:1][C@H:2]([C:4]([N:6]1[C:12](=[O:13])[CH:11]([CH3:14])[C:10]2[CH:15]=[CH:16][CH:17]=[CH:18][C:9]=2[C:8]2[C:19]([NH2:23])=[CH:20][CH:21]=[CH:22][C:7]1=2)=[O:5])[CH3:3])(=[O:36])=[O:35])[CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 3

HCID 1049PyridineHCID 754301-Butanesulfonyl chlorideHCID 697363355-(L-alaninyl)-amino-7-methyl-5,7-dihydro-6H-dibenz[b,d]azepin-6-one

Product 1

HCID 86592602HCID 86592602, compoundYield 342.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 5-(L-alaninyl)-amino-7-methyl-5,7-dihydro-6H-dibenz[b,d]azepin-6-one (Example 7B) (0.1500 g, 0.0485 mmol) in DMF (4 ml) were added pyridine (0.059 ml, 0.728 mmol) and 1-butanesulfonyl chloride (Aldrich) (0.063 ml, 0.485 mmol), stirred at RT overnight. The reaction mixture was evaporated to dryness. Water was added, extracted with EtOAc, washed with brine, dried over MgSO4. Evaporation and flash chromatography (silica, 5% MeOH/CH2Cl2), gave the title compound (0.0714 g, 34%) as a yellow solid.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. additionWater was added
  3. extractionextracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. customEvaporation and flash chromatography (silica, 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-9c3e427654ab496fab37b6d38da9fd42
Source dataset
uspto-grants-2003_05
Patent number
US06569851B1

Reaction notes

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