Benzenesulfonamide → N-[2,3,4,5-Tetrahydro-1-(1H-imidazol-4-yl-methyl)-4-(1-naphthalenylcarbonyl)-1H-1,4-benzodiazepin-8-yl]phenylsulfonamide, dihydrochloride

HRID 849394Notes

Reaction equation

HRID 849394 reaction equation
[C:1]1([S:7]([NH2:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:11].Cl.[NH:13]1[CH:17]=[C:16]([CH2:18][N:19]2[C:25]3[CH:26]=[C:27](N)[CH:28]=[CH:29][C:24]=3[CH2:23][N:22]([C:31]([C:33]3[C:42]4[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=4)[CH:36]=[CH:35][CH:34]=3)=[O:32])[CH2:21][CH2:20]2)[N:15]=[CH:14]1.C(N(CC)CC)C>C(Cl)Cl.C(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>[ClH:11].[ClH:11].[NH:13]1[CH:17]=[C:16]([CH2:18][N:19]2[C:25]3[CH:26]=[C:27]([NH:10][S:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)(=[O:9])=[O:8])[CH:28]=[CH:29][C:24]=3[CH2:23][N:22]([C:31]([C:33]3[C:42]4[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=4)[CH:36]=[CH:35][CH:34]=3)=[O:32])[CH2:21][CH2:20]2)[N:15]=[CH:14]1

Participants

7

Reactant 3

HCID 7370BenzenesulfonamideHCID 8471TriethylamineHCID 1784786502,3,4,5-Tetrahydro-1-(1H-imidazol-4-ylmethyl)-4-(1-naphthalenylcarbonyl)-8-amino-1H-1,4-benzodiazepine, dihydrochloride

Product 1

HCID 178478879N-[2,3,4,5-Tetrahydro-1-(1H-imidazol-4-yl-methyl)-4-(1-naphthalenylcarbonyl)-1H-1,4-benzodiazepin-8-yl]phenylsulfonamide, dihydrochloride

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Benzenesulphonamide (0.024 g, 0.13 mmol) was added to a solution of Example 26 (0.50 g, 0.12 mmol) and triethylamine (0.019 mL, 0.13 mmol) in CH2Cl2 (1 mL). After stirring for 16 hr, the reaction was diluted with CHCl3 (10 mL) and NaHCO3 (3 mL) and stirred for 30 min. The layers were separated and the aqueous layer was reextracted with CHCl3 (2×20 mL). The combined organic layers were dried over MgSO4, filtered and concentrated. The residue was treated with HCl/ether, a yellow solid was formed which was triturated with ether several times and dried under vacuum to afford Example 54 (0.64.2 g, 83%) as a light brown solid.

Workup

  1. stirringstirred for 30 min
  2. customThe layers were separated
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. additionThe residue was treated with HCl/ether
  7. customa yellow solid was formed which
  8. customwas triturated with ether several times
  9. customdried under vacuum
  10. customto afford Example 54 (0.64.2 g, 83%) as a light brown solid

Sources & evidence

ORD record
ord-9e36df183993489b999f8adf3c1c2424
Source dataset
uspto-grants-2000_01
Patent number
US06011029

Reaction notes

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