HCID 57961833, compound → HCID 57962423, compound

HRID 541821Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[C:11]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-])=O)[CH:20]=3)(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=2)[C:5]([Cl:28])=[CH:4][N:3]=1>O.CO.C(O)(=O)C.[Fe]>[NH2:25][C:21]1[CH:20]=[C:19]([S:16]([NH:15][C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([NH:8][C:6]3[C:5]([Cl:28])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=3)[CH:10]=2)(=[O:17])=[O:18])[CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution N-{3-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}-3-nitrobenzenesulfonamide (0.5 g, 1.0 mmol) in water (0.9 mL), methanol (4.4 mL) and acetic acid (1.7 mL) was added iron (250 mg, 4.5 mmol) powder in one portion. The mixture was stirred at 0° C. for 1 h and then mixed with celite and filtered. The crude cake was washed with EtOAc. The brown filtrate was concentrated and mixed with EtOAc and NaHCO3/water. The aqueous phase was extracted once with EtOAc. The organic phases were combined and dried over Na2SO4. The volatiles were removed under vacuum to give the desired product (0.45 g, 100%). LCMS for C16H13Cl2N5O2S (M+H)+: m/z=410.0, 411.9. 1H NMR (400 MHz, DMSO-d6): δ 9.57 (s, 1H), 9.42 (s, 1H), 8.33 (s, 1H), 8.16 (s, 1H), 7.91 (s, 1H), 7.29 (dd, J=7.9, 7.6 Hz, 1H), 7.15 (d, J=7.9 Hz, 1H), 7.10-7.05 (m, 2H), 6.90 (dd, J=8.2, 0.9 Hz, 1H), 6.84-6.81 (m, 1H), 4.11 (s, 2H).

Workup

additionmixed with celite and
filtrationfiltered
washThe crude cake was washed with EtOAc
concentrationThe brown filtrate was concentrated
additionmixed with EtOAc and NaHCO3/water
extractionThe aqueous phase was extracted once with EtOAc
dry with materialdried over Na2SO4
customThe volatiles were removed under vacuum

Sources & evidence

ORD record: ord-f7603bf4639a4558a67ec0ad843141a9
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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