Triethylamine → HCID 178513364, compound

HRID 2192283Notes

Reaction equation

[F:1][C:2]([F:30])([F:29])[C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([S:18]([C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH2:13][CH2:12]3)=[CH:5][CH:4]=1.Cl.[NH2:32][OH:33].C(N(CC)CC)C>O1CCCC1.CO>[OH:33][NH:32][C:25](=[NH:26])[C:24]1[CH:27]=[CH:28][C:21]([S:18]([N:14]2[C:15]3[C:11](=[CH:10][C:9]([C:6]4[CH:7]=[N:8][C:3]([C:2]([F:30])([F:29])[F:1])=[CH:4][CH:5]=4)=[CH:17][CH:16]=3)[CH2:12][CH2:13]2)(=[O:20])=[O:19])=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 90 °C

Procedure

223 mg 4-[5-(6-Trifluoromethyl-pyridin-3-yl)-2,3-dihydro-indole-1-sulfonyl]-benzonitrile were dissolved in a mixture of 8 ml tetrahydrofuran and 8 ml methanol. 902 mg hydroxylamine hydrochloride were added followed by the addition of 1.82 ml triethylamine. The reaction mixture was stirred at 90° C. for four hours. The solvents were removed in vacuo and the resulting residue poured into 50 ml water and extracted five times with portions of 50 ml ethylacetate. The combined organic extracts were washed with 100 ml brine, dried over MgSO4 and the solvent was evaporated in vacuo to obtain 550 mg crude N-Hydroxy-4-[5-(6-trifluoromethyl-pyridin-3-yl)-2,3-dihydro-indole-1-sulfonyl]-benzamidine. This material was used without further purification.

Workup

customThe solvents were removed in vacuo
additionthe resulting residue poured into 50 ml water
extractionextracted five times with portions of 50 ml ethylacetate
washThe combined organic extracts were washed with 100 ml brine
dry with materialdried over MgSO4
customthe solvent was evaporated in vacuo

Sources & evidence

ORD record: ord-b5d4001992454fb791e540f4feef83c4
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329725B2

Reaction notes

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