Triethylamine → 3-(5-chloro-2-methoxy-benzenesulfonylamino)-N-[4-(N-hydroxycarbamimidoyl)-phenyl]-benzamide

HRID 2241168Notes

Reaction equation

HRID 2241168 reaction equation
[ClH:1].[NH2:2][OH:3].C(N(CC)CC)C.Cl[C:12]1[CH:13]=[CH:14][C:15]([O:39][CH3:40])=[C:16]([S:18]([NH:21][C:22]2[CH:23]=[C:24]([CH:36]=[CH:37][CH:38]=2)[C:25]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][CH:29]=2)=[O:26])(=[O:20])=[O:19])[CH:17]=1>CS(C)=O.O>[Cl:1][C:12]1[CH:13]=[CH:14][C:15]([O:39][CH3:40])=[C:16]([S:18]([NH:21][C:22]2[CH:23]=[C:24]([CH:36]=[CH:37][CH:38]=2)[C:25]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([C:34](=[NH:35])[NH:2][OH:3])=[CH:30][CH:29]=2)=[O:26])(=[O:19])=[O:20])[CH:17]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 67548905HCID 67548905, compound

Product 1

HCID 1784907253-(5-chloro-2-methoxy-benzenesulfonylamino)-N-[4-(N-hydroxycarbamimidoyl)-phenyl]-benzamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

Hydroxylamine hydrochloride (0.24 mg, 3 mmol) was suspended in dimethyl sulfoxide under an argon atmosphere. Triethylamine (0.34 g, 3 mmol) was added dropwise. The mixture was stirred at room temperature for 15 min then filtered, washing with dry tetrahydrofuran. The filtrate was concentrated under vacuum. The resulting solution in dimethyl sulfoxide was treated with 3-(5-chloro-2-methoxy-benzenesulfonylamino)-N-(4-cyano-phenyl)-benzamide (0.30 g, 0.68 mmol) and the mixture was warmed to 75° C. and stirred for 2 hours. The mixture was cooled to room temperature then diluted with water and extracted with ethyl acetate. The organic phase was extracted with HCl 0.5 N. The heterogeneous aqueous solution was adjusted to pH 9-10 with NaOH 0.5N, then extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and evaporated to yield 3-(5-chloro-2-methoxy-benzenesulfonylamino)-N-[4-(N-hydroxycarbamimidoyl)-phenyl]-benzamide as a light green solid, MS (ISP): m/e=473.2 (M−H), which was used as such in the following reaction (0.23 g, 73%)

Workup

  1. filtrationthen filtered
  2. washwashing with dry tetrahydrofuran
  3. concentrationThe filtrate was concentrated under vacuum
  4. temperaturethe mixture was warmed to 75° C.
  5. stirringstirred for 2 hours
  6. temperatureThe mixture was cooled to room temperature
  7. extractionextracted with ethyl acetate
  8. extractionThe organic phase was extracted with HCl 0.5 N
  9. extractionextracted with ethyl acetate
  10. dry with materialThe combined organic phases were dried over sodium sulfate
  11. customevaporated

Sources & evidence

ORD record
ord-a50194ff06ad4072b54e04908cf27c67
Source dataset
uspto-grants-2010_05
Patent number
US07723538B2

Reaction notes

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