Triethylamine → HCID 178480431, compound

HRID 2270923Notes

Reaction equation

HRID 2270923 reaction equation
[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]2[CH:14]=[CH:13][C:12]([N:15]([CH2:20][C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][C:25]([C:31]#[N:32])=[CH:26][CH:27]=4)[CH:22]=3)[S:16]([NH2:19])(=[O:18])=[O:17])=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.C(N(CC)CC)C.[ClH:40].[NH2:41][OH:42]>C(O)C>[Cl-:40].[Cl-:40].[Cl-:40].[OH:42][NH:41][C:31]([C:25]1[CH:24]=[C:23]2[C:28]([CH:29]=[CH:30][C:21]([CH2:20][N:15]([C:12]3[CH:11]=[CH:10][C:9]([N:5]4[CH2:6][CH2:7][CH2:8][N:2]([CH3:1])[CH2:3][CH2:4]4)=[CH:14][CH:13]=3)[S:16]([NH2:19])(=[O:18])=[O:17])=[CH:22]2)=[CH:27][CH:26]=1)=[NH:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 70246026HCID 70246026, compound

Product 1

HCID 178480431HCID 178480431, compoundYield 16.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

230 mg of N-(4-(4-methylhexahydro-1H-1,4-diazepin-1-yl)phenyl]-N-[(7-cyano-2-naphthyl)methyl]sulfamide was dissolved in 9.2 ml of ethanol, to which were added 0.25 ml of triethylamine and 90 mg of hydroxylamine hydrochloride. The mixture was heated for reflux for 2 hours. The reaction mixture was evaporated, and the resulting residue was purified through silica gel column chromatography using an eluent solvent of concentrated ammonia water/methanol/chloroform (0.1/1/7). The solvent was evaporated, and a small amount of aqueous 1 N hydrochloric acid was to the residue, and then evaporated again in vacuo, to obtain 41 mg of N-[(7-hydroxyamidino-2-naphthyl)methyl]-N-[4-(4-methylhexa-hydro-1H-1,4-diazepin-1-yl)phenyl]sulfamide trichloride.

Workup

  1. temperatureThe mixture was heated
  2. temperaturefor reflux for 2 hours
  3. customThe reaction mixture was evaporated
  4. customthe resulting residue was purified through silica gel column chromatography
  5. customThe solvent was evaporated
  6. customevaporated again in vacuo

Sources & evidence

ORD record
ord-a38aa2bd42174ab49816ee1a3b288244
Source dataset
uspto-grants-2001_12
Patent number
US06333320B1

Reaction notes

Loading…