Water → N-[4-(6-{[(1S)-1-Phenylethyl]amino}pyrazin-2-yl)phenyl]methanesulfonamide

HRID 1244409Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([NH:14][C@H:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:16])[CH:11]=[N:10][CH:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32].O>C1COCC1>[C:17]1([C@@H:15]([NH:14][C:12]2[N:13]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][S:31]([CH3:30])(=[O:33])=[O:32])=[CH:7][CH:6]=3)[CH:9]=[N:10][CH:11]=2)[CH3:16])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 6-(4-aminophenyl)-N-[(1S)-1-phenylethyl]pyrazin-2-amine (58 mg, 0.2 mmol) in dry THF (3 mL) was added triethylamine (70 μL, 0.5 mmol). The solutions was cooled to 0° C. and methanesulphonyl chloride (18.6 μL, 0.24 mmol) was added dropwise. The mixture was allowed to warm to RT and stirred overnight, before dilution with water (15 mL). The product was extracted into ethyl acetate (2×15 mL) and the combined extracts washed with 10% aqueous Na2CO3 and brine, and then dried (Na2SO4). The solvent was removed under reduced pressure and the product purified by chromatography eluting with ethyl acetate-hexane (3:2) to afford the product as a pale yellow solid (54 mg, 73%).

Workup

temperatureto warm to RT
extractionThe product was extracted into ethyl acetate (2×15 mL)
washthe combined extracts washed with 10% aqueous Na2CO3 and brine
dry with materialdried (Na2SO4)
customThe solvent was removed under reduced pressure
customthe product purified by chromatography
washeluting with ethyl acetate-hexane (3:2)

Sources & evidence

ORD record: ord-bca8734e607549a29d525598cf33a01d
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07122550B2

Reaction notes

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