4-Fluoro-phenylsulfamoyl chloride → N-{2-[(1R)-2,3-dihydro-1H-inden-1-ylamino]quinolin-5-yl}-N'-(4-fluorophenyl)sulfamide

HRID 2076331Notes

Reaction equation

[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:17]([NH2:21])=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[F:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][S:30](Cl)(=[O:32])=[O:31])=[CH:25][CH:24]=1>N1C=CC=CC=1>[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[NH:21][S:30]([NH:29][C:26]3[CH:25]=[CH:24][C:23]([F:22])=[CH:28][CH:27]=3)(=[O:31])=[O:32])[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 45 °C

Procedure

(R)—N2-Indan-1-yl-quinoline-2,5-diamine (example 43, step A+B, 200 mg, 0.727 mmol) was dissolved in 3 mL pyridine and 4-fluoro-phenylsulfamoyl chloride (298 mg, 1.42 mmol) was added. The reaction mixture was stirred at 45° C. for 2 days and quenched by addition of 50 mL water. The mixture was extracted three times with ethyl acetate (50 mL each). The organic phases ware pooled, dried with sodium sulfate, filtered and evaporated. The residue was purified by flash chromatography on silica gel (heptane, tetrahydrofurane 100:0->50:50 gradient). The title compound was obtained as a brown solid (43 mg, 13%), MS: m/e=449.1 (M+H+).

Workup

customquenched by addition of 50 mL water
extractionThe mixture was extracted three times with ethyl acetate (50 mL each)
dry with materialdried with sodium sulfate
filtrationfiltered
customevaporated
customThe residue was purified by flash chromatography on silica gel (heptane, tetrahydrofurane 100:0->50:50 gradient)

Sources & evidence

ORD record: ord-23cbfb20da904816914a65e3eef78316
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07923561B2

Reaction notes

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