Pyridine → HCID 19957044, compound

HRID 1769142Notes

Reaction equation

HRID 1769142 reaction equation
Cl.Cl.[CH3:3][N:4]1[C:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)=[N:9][CH:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:7]2[CH:25]=[CH:26][CH:27]=[CH:28][C:6]=2[CH2:5]1.C(Cl)Cl.N1C=CC=CC=1.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>C(OC)(C)(C)C.O>[CH3:3][N:4]1[C:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][S:39]([CH3:38])(=[O:41])=[O:40])=[CH:14][CH:13]=2)=[N:9][CH:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:7]2[CH:25]=[CH:26][CH:27]=[CH:28][C:6]=2[CH2:5]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 19957080HCID 19957080, compound

Product 1

HCID 19957044HCID 19957044, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a cooled mixture of the diamine dihydrochloride of Example 378 (b) (1.16 g, 28 mmol), CH2Cl2 (25 mL) and pyridine (6 mL) under nitrogen was added methanesulfonyl chloride (0.64 g, 56 mmol). The reaction mixture was stirred, with cooling in ice-bath, for 13/4 hours and then was poured into a solution of water/saturated Na2CO3. The layers were separated, the aqueous layer was extracted with CH2Cl2, and the organic layers were combined and washed with water/saturated Na2CO3. The organic layer was dried over Na2SO4, the solvent was removed in vacuo, and the residue was diluted with hexane. A precipitate formed which was slurried with t-BuOMe and collected by filtration. The solid was recrystallized from hot CH2Cl2 /hexane to afford 0.85 g (73%) of 4,5-dihydro-4-methyl-1-phenyl-3-[1-(4-methylsulfonylaminophenyl)methyl]-1H-2,4-benzodiazepine as an off-white solid, m.p. 182°-185° C.

Workup

  1. temperaturewith cooling in ice-bath
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. washwashed with water/saturated Na2CO3
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customthe solvent was removed in vacuo
  7. additionthe residue was diluted with hexane
  8. customA precipitate formed which
  9. filtrationcollected by filtration
  10. customThe solid was recrystallized from hot CH2Cl2 /hexane

Sources & evidence

ORD record
ord-eeb3983d65354fdb82a22a3f384181bd
Source dataset
uspto-grants-1995_01
Patent number
US05380721

Reaction notes

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