N-(2-acetyl-5-methoxyphenyl)-4-Isopropyl-2-Thiazolecarboxamide → HCID 178487691, compound

HRID 925941Notes

Reaction equation

HRID 925941 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[NH:12][C:13]([C:15]1[S:16][CH:17]=[C:18]([CH:20]([CH3:22])[CH3:21])[N:19]=1)=O)(=[O:3])[CH3:2].CC(C)([O-])C.[K+]>CC(O)(C)C>[CH:20]([C:18]1[N:19]=[C:15]([C:13]2[CH:2]=[C:1]([OH:3])[C:4]3[C:5](=[CH:6][C:7]([O:10][CH3:11])=[CH:8][CH:9]=3)[N:12]=2)[S:16][CH:17]=1)([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 20773655N-(2-acetyl-5-methoxyphenyl)-4-Isopropyl-2-ThiazolecarboxamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 178487691HCID 178487691, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of compound 217a (4.312 g, 1 eq.) in tBuOH (60 mL) was added potassium t-butoxide (3.8 g, 2.5 eq.) under nitrogen. The mixture was stirred at 70° C. for 16 hrs, and then cooled down to 0° C. and quenched with MeOH (10 mL) and acetic acid (2.5 mL). The solvent was removed under reduced pressure and the residue was triturated in a mixture of MeOH/water, isolated by filtration, washed with ACN, and then petroleum ether to yield compound 218a as a yellow solid in 71% yield. 1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.32 (d, J=6.98 Hz, 6H), 3.14 (m, 1H), 3.89 (s, 3H), 7.06 (br s, 1H), 7.50-7.66 (m, 3H), 8 (d, J=9.05 Hz, 1H), 11.62 (br s, 1H); MS (ESI, EI+): m/z=301 (MH+).

Workup

  1. temperaturecooled down to 0° C.
  2. customquenched with MeOH (10 mL) and acetic acid (2.5 mL)
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was triturated in a mixture of MeOH/water
  5. customisolated by filtration
  6. washwashed with ACN

Sources & evidence

ORD record
ord-549a1f5eb6994d90853e9ae4a530d8ac
Source dataset
uspto-grants-2016_03
Patent number
US09284307B2

Reaction notes

Loading…