3-Bromocyclohexane-1,2-dione → 2-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylamino)-6,7-dihydrobenzo[d]thiazol-4(5H)-one

HRID 1803269Notes

Reaction equation

HRID 1803269 reaction equation
Br[CH:2]1[CH2:7][CH2:6][CH2:5][C:4](=O)[C:3]1=[O:9].[CH3:10][O:11][C:12]1[CH:13]=[C:14]([NH:24][C:25]([NH2:27])=[S:26])[CH:15]=[CH:16][C:17]=1[N:18]1[CH:22]=[N:21][C:20]([CH3:23])=[N:19]1>C(O)C.CCOC(C)=O>[CH3:10][O:11][C:12]1[CH:13]=[C:14]([NH:24][C:25]2[S:26][C:7]3[CH2:6][CH2:5][CH2:4][C:3](=[O:9])[C:2]=3[N:27]=2)[CH:15]=[CH:16][C:17]=1[N:18]1[CH:22]=[N:21][C:20]([CH3:23])=[N:19]1

Participants

5

Reactant 2

HCID 134385013-Bromocyclohexane-1,2-dioneHCID 866498981-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)thiourea

Product 1

HCID 866499272-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylamino)-6,7-dihydrobenzo[d]thiazol-4(5H)-oneYield 44%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-bromocyclohexane-1,2dione (158 mg, 0.827 mmol, from preparation AAE) and 1-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)thiourea (109 mg, 0.414 mmol, from step 4 of preparation F) was heated in ethanol (1.4 mL) at 80° C. for 12 h. The crude reaction was diluted with EtOAc and washed with saturated sodium bicarbonate solution. The organic layer was concentrated in vacuo. The crude product was purified using preparatory TLC (80% acetone/hexanes) to afford 2-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylamino)-6,7-dihydrobenzo[d]thiazol-4(5H)-one (64 mg, 44% yield) as a yellow solid. LC-MS (M+H)+ 356.3. 1H NMR (400 MHz, chloroform-d) δ ppm 8.55 (s, 1 H) 7.68 (d, J=8.56 Hz, 1 H) 7.31 (d, J=2.27 Hz, 1 H) 6.96 (dd, J=8.56, 2.52 Hz, 1 H) 3.95 (s, 3H) 3.00 (t, J=6.04 Hz, 2 H) 2.59-2.68 (m, 2 H) 2.45-2.52 (m, 3H) 2.20-2.31 (m, 2H).

Workup

  1. customThe crude reaction
  2. washwashed with saturated sodium bicarbonate solution
  3. concentrationThe organic layer was concentrated in vacuo
  4. customThe crude product was purified

Sources & evidence

ORD record
ord-6c147d0da6944f0491aa71fe5b00fe1a
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

Loading…