Sulfuric acid magnesium salt (1:1) → HCID 13649559, compound

HRID 1982394Notes

Reaction equation

HRID 1982394 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]2[C:12]3[CH:23]=[CH:22][CH:21]=[CH:20][C:13]=3[CH2:14][N:15]3[CH:19]=[CH:18][CH:17]=[C:16]3[C:10]2=[N:9][N:8]=1.[Br:24]N1C(=O)CCC1=O.S(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1.C(Cl)Cl>[Br:24][C:19]1[N:15]2[C:16]([C:10]3[N:11]([C:7]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)=[N:8][N:9]=3)[C:12]3[CH:23]=[CH:22][CH:21]=[CH:20][C:13]=3[CH2:14]2)=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 67184N-bromobutanimideHCID 13649490HCID 13649490, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 13649559HCID 13649559, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 3 g of 3-(2-pyridinyl)-9H-pyrrolo[2,1-c]-1,2,4-triazolo[4,3-a][1,4]benzodiazepine in 50 mL of tetrahydrofuran is added 1.8 g of N-bromosuccinimide. The reaction mixture is allowed to stir at room temperature for 3 hours during which time a heavy white precipitate forms. A solution of aqueous sodium bisulfite is added to the reaction mixture and, after stirring for an additional 1 hour, the solid is collected and washed with 100 ml of water. The filtrate is evaporated to dryness under reduced pressure to yield a white solid. The combined solids are dissolved in 150 mL of methylene chloride, the solution is drived over anhydrous magnesium sulfate, filtered, and the solvent is evaporated under reduced pressure to yield 11-bromo-3-(2-pyridinyl)-9H-pyrrolo[2,1-c]-1,2,4-triazolo[4,3-a][1,4]benzodiazepine, m.p. 228°-229° (d). Product is recrystallized from a mixture of methylene chloride and diethyl ether.

Workup

  1. stirringafter stirring for an additional 1 hour
  2. customthe solid is collected
  3. washwashed with 100 ml of water
  4. customThe filtrate is evaporated to dryness under reduced pressure
  5. customto yield a white solid
  6. filtrationfiltered
  7. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-bea286ba6212492599126a04e6a5b0f1
Source dataset
uspto-grants-1986_06
Patent number
US04596799

Reaction notes

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