Pyridine → HCID 86592600, compound

HRID 413870Notes

Reaction equation

HRID 413870 reaction equation
Cl.[NH2:2][C@H:3]([C:5]([N:7]1[C:13](=[O:14])[CH:12]([CH3:15])[C:11]2[CH:16]=[CH:17][CH:18]=[CH:19][C:10]=2[C:9]2[C:20]([NH2:24])=[CH:21][CH:22]=[CH:23][C:8]1=2)=[O:6])[CH3:4].N1C=CC=CC=1.[F:31][C:32]1[CH:33]=[C:34]([S:38](Cl)(=[O:40])=[O:39])[CH:35]=[CH:36][CH:37]=1>C1COCC1>[F:31][C:32]1[CH:33]=[C:34]([S:38]([NH:2][C@H:3]([C:5]([N:7]2[C:13](=[O:14])[CH:12]([CH3:15])[C:11]3[CH:16]=[CH:17][CH:18]=[CH:19][C:10]=3[C:9]3[C:20]([NH2:24])=[CH:21][CH:22]=[CH:23][C:8]2=3)=[O:6])[CH3:4])(=[O:40])=[O:39])[CH:35]=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 27342583-Fluorobenzenesulfonyl ChlorideHCID 69737332HCID 69737332, compound

Product 1

HCID 86592600HCID 86592600, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 5-(L-alaninyl)-amino-7-methyl-5,7-dihydro-6H-dibenz[b,d]azepin-6-one hydrochloride (Example 7B) (0.1500 g, 0.434 mmol) in THF (4 ml) was added pyridine (0.088ml, 1.09 mmol) and 3-fluorobenzenesulfonyl chloride (Fluorochem Limited) (0.0928 ml, 0.477 mmol), stirred at RT overnight. The reaction mixture was evaporated to dryness. Water was added, filtered. The solid was purified with flash chromatography (silica, 6% MeOH/CH2Cl2, crystallized with CH2Cl2/hexane and washed with Et2O/hexane (1:1, v/v) to give the title compound (0.0580 g, 29%) as a white solid.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. additionWater was added
  3. filtrationfiltered
  4. customThe solid was purified with flash chromatography (silica, 6% MeOH/CH2Cl2
  5. customcrystallized with CH2Cl2/hexane
  6. washwashed with Et2O/hexane (1:1

Sources & evidence

ORD record
ord-00e568f84f414aeba256deca10120302
Source dataset
uspto-grants-2003_05
Patent number
US06569851B1

Reaction notes

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