1-Bromo-3-(4-chlorophenyl)propan-2-one → 4-[4-(4-Chloro-benzyl)-thiazol-2-ylamino]-2-fluoro-N-thiazol-2-yl-benzenesulfonamide

HRID 1644629Notes

Reaction equation

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

Participants

Conditions

Temperature: 95 °C

Procedure

The mixture of the 2-fluoro-N-thiazol-2-yl-4-thioureido-benzenesulfonamide (32 mg, 0.000048 mol) and 1-bromo-3-(4-chloro-phenyl)-propan-2-one (14 mg, 0.000058 mol) in DMF/AcOH (1:1) was heated at 95° C. for 20 min. The crude product was purified using Gilson preparative HPLC (reverse phase, Phenomenex 250×30 min, 15 micron C18 column, 40 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). Fractions were checked by LC/MS. The appropriate fractions were combined and dried on a lyophilizer to give the desired product as a light yellow powder (10.8 mg, 47%).

Workup

customThe crude product was purified
customGilson preparative HPLC (reverse phase, Phenomenex 250×30 min, 15 micron C18 column, 40 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)
customdried on a lyophilizer

Sources & evidence

ORD record: ord-0a94fe09478e4bfa9393233dffb43a96
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08124610B2

Reaction notes

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