Stannous Chloride → 3-Amino-N-[5-(5-bromo-2-chloro-pyrimidin-4-ylamino)-pentyl]-benzenesulfonamide

HRID 970415Notes

Reaction equation

[Br:1][C:2]1[C:3]([NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-])=O)[CH:20]=2)(=[O:18])=[O:17])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[Sn](Cl)Cl.C([O-])(O)=O.[Na+]>C(O)C>[NH2:25][C:21]1[CH:20]=[C:19]([S:16]([NH:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][NH:9][C:3]2[C:2]([Br:1])=[CH:7][N:6]=[C:5]([Cl:8])[N:4]=2)(=[O:17])=[O:18])[CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 300 mg (0.63 mmol) of N-[5-(5-bromo-2-chloro-pyrimidin-4-ylamino)-pentyl]-3-nitro-benzenesulfonamide in 6 ml of ethanol is mixed with 600 mg of tin(II) chloride and stirred for 30 minutes at 70° C. After cooling, the reaction mixture is carefully added to ice water and made basic with saturated NaHCO3 solution. It is extracted with ethyl acetate (3×). The combined organic phases are dried (Na2SO4), filtered, and concentrated by evaporation. The remaining residue is purified by chromatography (ethyl acetate/hexane 4:1). 112 mg (0.25 mmol, corresponding to 40% of theory) of the product is obtained.

Workup

temperatureAfter cooling
extractionIt is extracted with ethyl acetate (3×)
dry with materialThe combined organic phases are dried (Na2SO4)
filtrationfiltered
concentrationconcentrated by evaporation
customThe remaining residue is purified by chromatography (ethyl acetate/hexane 4:1)
custom112 mg (0.25 mmol, corresponding to 40% of theory) of the product is obtained

Sources & evidence

ORD record: ord-0dc253ed2bf842c8be55fc6e01f98a2e
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07312225B2

Reaction notes

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