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

HRID 1803270Notes

Reaction equation

HRID 1803270 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([NH:23][C:24]2[S:25][C:26]3[CH2:32][CH2:31][CH2:30][C:29](=[O:33])[C:27]=3[N:28]=2)[CH:14]=[CH:15][C:16]=1[N:17]1[CH:21]=[N:20][C:19]([CH3:22])=[N:18]1>C(OCC)C>[CH3:9][O:10][C:11]1[CH:12]=[C:13]([NH:23][C:24]2[S:25][C:26]3[CH2:32][CH2:31][CH2:30][C:29]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)([OH:33])[C:27]=3[N:28]=2)[CH:14]=[CH:15][C:16]=1[N:17]1[CH:21]=[N:20][C:19]([CH3:22])=[N:18]1

Participants

4

Reactant 2

HCID 866499272-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylamino)-6,7-dihydrobenzo[d]thiazol-4(5H)-oneHCID 178418255HCID 178418255, compound

Product 1

HCID 581100282-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylamino)-4-phenyl-4,5,6,7-tetrahydrobenzo[d]thiazol-4-olYield 59.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Phenylmagnesium bromide (1.0 M in THF, 0.118 mL, 0.118 mmol) was added to a rt solution of 2-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylamino)-6,7-dihydrobenzo[d]thiazol-4(5H)-one (14 mg, 0.039 mmol) in diethyl ether (0.13 mL). The reaction was quenched with saturated ammonium chloride and extracted with EtOAc. The organic layer was concentrated in vacuo. The crude product was purified using preparatory TLC (60% acetone/hexanes) to afford 10 mg (53% yield) of the titled compound as a oil. LC-MS (M+H)+ 434.3.

Workup

  1. customThe reaction was quenched with saturated ammonium chloride
  2. extractionextracted with EtOAc
  3. concentrationThe organic layer was concentrated in vacuo
  4. customThe crude product was purified

Sources & evidence

ORD record
ord-1e79eb94685a40b6ac759108977c3707
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

Loading…