Triethylamine → 10,11-Dihydro-10-[3-methoxy-4-[(butylsulfonyl)amino]benzoyl]-5H-pyrrolo[2,1-c][1,4]benzodiazepine

HRID 55256

Reaction equation

HRID 55256 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][N:11]3[CH:19]=[CH:20][CH:21]=[C:10]3[CH2:9]2)=[O:7])=[CH:4][C:3]=1[O:24][CH3:25].C(N(CC)CC)C.[CH2:33]([S:37](Cl)(=[O:39])=[O:38])[CH2:34][CH2:35][CH3:36]>C(Cl)Cl>[CH3:25][O:24][C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][C:2]=1[NH:1][S:37]([CH2:33][CH2:34][CH2:35][CH3:36])(=[O:39])=[O:38])[C:6]([N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12][N:11]2[CH:19]=[CH:20][CH:21]=[C:10]2[CH2:9]1)=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 754301-Butanesulfonyl chlorideHCID 10806563(4-amino-3-methoxy-phenyl)[10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl]methanone

Product 1

HCID 2183700810,11-Dihydro-10-[3-methoxy-4-[(butylsulfonyl)amino]benzoyl]-5H-pyrrolo[2,1-c][1,4]benzodiazepineYield 102.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 0.10 g of 10,11-dihydro-10-(4-amino-3-methoxybenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 2 ml of methylene chloride is added 60 mg of triethylamine followed by a solution of 56 mg of n-butylsulfonyl chloride in 0.5 ml of methylene chloride. After stirring at room temperature for 2 hours, the reaction mixture is evaporated in vacuo to a residue which is dissolved in methyl alcohol, stirred for 1 hour and evaporated in vacuo to a residue which is treated with 2 ml of NH4Cl and extracted with 15 ml of ethyl acetate. The organic: extract is washed with saturated NaHCO3, brine, dried (Na2SO4), filtered through hydrous magnesium silicate and the filtrate evaporated to a residue. The residue is stirred with ether-hexanes to give 0.14 g of light yellow solid. MS (CI): 454(M+H).

Workup

  1. customthe reaction mixture is evaporated in vacuo to a residue which
  2. dissolutionis dissolved in methyl alcohol
  3. stirringstirred for 1 hour
  4. customevaporated in vacuo to a residue which
  5. additionis treated with 2 ml of NH4Cl
  6. extractionextracted with 15 ml of ethyl acetate
  7. extractionThe organic: extract
  8. washis washed with saturated NaHCO3, brine
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered through hydrous magnesium silicate
  11. customthe filtrate evaporated to a residue
  12. stirringThe residue is stirred with ether-hexanes

Sources & evidence

ORD record
ord-e2d6d75fb7854c73980546a09683eb46
Source dataset
uspto-grants-1997_04
Patent number
US05624923

Linked notes

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