3-Pentanamine → 6-Chloro-N-ethyl-3-[2-(1-ethyl-propylamino)-3,4-dioxo-cyclobut-1-enylamino]-2-hydroxy-N-methoxy-benzenesulfonamide

HRID 516907Notes

Reaction equation

[Cl:1][C:2]1[C:7]([S:8]([N:11]([O:14][CH3:15])[CH2:12][CH3:13])(=[O:10])=[O:9])=[C:6]([OH:16])[C:5]([NH:17][C:18]2[C:21](=O)[C:20](=[O:23])[C:19]=2[O:24]CC)=[CH:4][CH:3]=1.[NH2:27][CH:28]([CH2:31][CH3:32])[CH2:29][CH3:30]>C1COCC1>[Cl:1][C:2]1[C:7]([S:8]([N:11]([CH2:12][CH3:13])[O:14][CH3:15])(=[O:9])=[O:10])=[C:6]([OH:16])[C:5]([NH:17][C:18]2[C:19](=[O:24])[C:20](=[O:23])[C:21]=2[NH:27][CH:28]([CH2:31][CH3:32])[CH2:29][CH3:30])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of 6-Chloro-3-(2-ethoxy-3,4-dioxo-cyclobut-1-enylamino)-2-hydroxy-N-methoxy-N-ethyl-benzenesulfonamide (Intermediate FA) (100 mg, 0.25 mmol) in THF (2 ml) was added 3-aminopentane (29 mg, 0.25 mmol) The reaction mixture was heated at 50° C. overnight. Further 3-aminopentane (29 mg, 0.25 mmol) was added and the reaction was heated at 50° C. for 7 hours. The reaction mixture was concentrated in vacuo and dissolved in EtOAc. The EtOAc solution was washed with 10% citric acid (aq), brine, dried (sodium sulfate) and concentrated in vacuo to give a solid; [M+H]+ 446.1. 1H NMR (DMSO) 0.9 (6H, t, 2×CH3), 1.2 (3H, t, CH3), 1.5 (2H, m), 1.6 (2H, m), 3.3 (2H, m), 3.7 (3H, s, CH3) 3.9 (1H, m), 7.2 (1H, d), 8.1 (1H, d), 8.3 (1H, d), 9.4 (1H, s), 10.2 (1H, s).

Workup

temperaturethe reaction was heated at 50° C. for 7 hours
concentrationThe reaction mixture was concentrated in vacuo
dissolutiondissolved in EtOAc
washThe EtOAc solution was washed with 10% citric acid (aq), brine
dry with materialdried (sodium sulfate)
concentrationconcentrated in vacuo
customto give a solid

Sources & evidence

ORD record: ord-90a3a808f1bb4bccb1bf1d4c8580c29a
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115087B2

Reaction notes

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