4-(4-Methoxybenzyloxy)-8-chloro-7-methoxy-2-(4-methylthiazol-2-yl)quinoline → HCID 178487695, compound

HRID 880798Notes

Reaction equation

HRID 880798 reaction equation
COC1C=CC(C[O:8][C:9]2[C:18]3[C:13](=[C:14]([Cl:21])[C:15]([O:19][CH3:20])=[CH:16][CH:17]=3)[N:12]=[C:11]([C:22]3[S:23][CH:24]=[C:25]([CH3:27])[N:26]=3)[CH:10]=2)=CC=1>FC(F)(F)C(O)=O>[Cl:21][C:14]1[C:15]([O:19][CH3:20])=[CH:16][CH:17]=[C:18]2[C:13]=1[N:12]=[C:11]([C:22]1[S:23][CH:24]=[C:25]([CH3:27])[N:26]=1)[CH:10]=[C:9]2[OH:8]

Participants

3

Reactant 1

HCID 578167174-(4-Methoxybenzyloxy)-8-chloro-7-methoxy-2-(4-methylthiazol-2-yl)quinoline

Product 1

HCID 178487695HCID 178487695, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Compound 275 (750 mg, 1 eq.) in trifluoroacetic acid (5 mL) was stirred at room temperature for 10 min. Then, the acid was evaporated, ethyl acetate added and concentrated again in diminished pressure. The residue was triturated in diethyl ether to give the compound 276 as a white solid in quantitative yield. 1H NMR (CDCl3, 400 MHz) δ (ppm) 2.59 (d, J=0.81 Hz, 3H), 4.10 (s, 3H), 7.19 (d, J=9.25 Hz, 1H), 7.22 (d, J=0.81 Hz, 1H), 7.25 (s, 1H), 8.36 (d, J=9.25 Hz, 1H), 10.51 (br s, 1H); MS (ESI, EI+): m/z=306.93 (MH+).

Workup

  1. customThen, the acid was evaporated
  2. additionethyl acetate added
  3. concentrationconcentrated again in diminished pressure
  4. customThe residue was triturated in diethyl ether

Sources & evidence

ORD record
ord-1f851b6e13be41d584711e24bb5f2416
Source dataset
uspto-grants-2015_03
Patent number
US08993595B2

Reaction notes

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