3-Bromocyclohexane-1,2-dione → 2-[4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-6,7-dihydro-5H-benzothiazol-4-one

HRID 1433073Notes

Reaction equation

HRID 1433073 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([S:10]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][C:20]([NH2:22])=[S:21])[CH2:15][CH2:14]3)(=[O:12])=[O:11])[S:7][C:6]=2[CH:23]=1.Br[CH:25]1[CH2:30][CH2:29][CH2:28][C:27](=[O:31])[C:26]1=O.C1(C)C=CC=CC=1.C([OH:44])(C)(C)C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([S:10]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][C:20]4[S:21][C:25]5[CH2:30][CH2:29][CH2:28][C:27](=[O:31])[C:26]=5[N:22]=4)[C:15](=[O:44])[CH2:14]3)(=[O:11])=[O:12])[S:7][C:6]=2[CH:23]=1

Participants

4

Reactant 3

HCID 134385013-Bromocyclohexane-1,2-dioneHCID 22595558Toluene tert-butyl alcoholHCID 865925602-[4-(6-Chloro-benzo[b]thiophene-2-sulfonyl)-piperazin-1-yl]-thioacetamide

Product 1

HCID 670150242-[4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-6,7-dihydro-5H-benzothiazol-4-one

Conditions

Temperature
90 °C

Procedure

To a solution of toluene/t-butanol (1:1) is added 2-[4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-piperazin-1-yl]-thioacetamide (180 mg, 0.45 mmol) and 3-bromo-cyclohexane-1,2-dione (135 mg, 0.80 mmol). The reaction is heated at 90° C. for 4 h and is then concentrated and crude product is dissolved in CH2Cl2 and washed with NaHCO3. The solution is concentrated and purified using 1% MeOH/EtOAc to provide 2-[4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-6,7-dihydro-5H-benzothiazol-4-one. 1H NMR (300 MHz, CDCl3) δ7.87-7.82 (m, 3H), 7.47 (dd, 1H), 4.80 (s, 2H), 3.91 (s, 2H), 3.61 (t, 2H), 3.43 (t, 2H), 3.05 (t, 2H), 2.65 (t, 2H), 2.24 (dt, 2H); MS (Ion Spray) 496 (M+H)+.

Workup

  1. concentrationis then concentrated
  2. dissolutioncrude product is dissolved in CH2Cl2
  3. washwashed with NaHCO3
  4. concentrationThe solution is concentrated
  5. custompurified

Sources & evidence

ORD record
ord-52d82111800c4ee680c93843e87ac701
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

Loading…