1-Bromo-3-(4-chlorophenyl)propan-2-one → 6-(4-(4-chlorobenzyl)thiazol-2-ylamino)-N-(thiazol-2-yl)pyridine-3-sulfonamide

HRID 1644662Notes

Reaction equation

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

Participants

Conditions

Temperature: 95 °C

Procedure

The mixture of the 6-Thioureido-pyridine-3-sulfonic acid thiazol-2-ylamide (27 mg, 0.000086 mol) and 1-Bromo-3-(4-chloro-phenyl)-propan-2-one (25 mg, 0.00010 mol) in DMF/AcOH (1:1) was heated at 95° C. for 20 min. The reaction solution was directly purified on Gilson (semi-prep, reverse phase, Phenomenex 100×21.2 mm 10 micron C18 column, 20 mL/min, Gradient 85% A to 100% B over 25 min. Solvent A: 7800 water/200 acetonitrile/8 TFA. Solvent B: 7200 acetonitrile/800 water/8 TFA). Fractions were checked by LC/MS and found no pure desired product was isolated. Fractions with the desired product were combined and then dried on a lyophilizer to give the product (1126-8-P1) as a yellow powder. The product (a mixture) was purified again by chromatography (silica gel, 5% Ethyl acetate in hexanes to 100% Ethyl acetate) to give a cleaner product (1126-8-P2), which was purified by Prep TLC (25% Ethyl acetate in hexanes, then 100% Ethyl acetate) to give the final pure product (1126-8-P-3) as a yellow solid.

Workup

customThe reaction solution was directly purified on Gilson (semi-prep, reverse phase, Phenomenex 100×21.2 mm 10 micron C18 column, 20 mL/min, Gradient 85% A to 100% B over 25 min. Solvent A: 7800 water/200 acetonitrile/8 TFA. Solvent B: 7200 acetonitrile/800 water/8 TFA)
customwas isolated

Sources & evidence

ORD record: ord-64a10103578b4fbab00929b30524509c
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08124610B2

Reaction notes

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