p-Toluenesulfonic acid → HCID 24851913, compound

HRID 2381066Notes

Reaction equation

HRID 2381066 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:12]1([O:17][C:18]2[C:19]([O:47][CH3:48])=[CH:20][CH:21]=[C:22]3[C:27]=2[N:26]([CH2:28][CH2:29][O:30]C2CCCCO2)[C:25](=[O:37])[CH:24]=[C:23]3[NH:38][C:39]2[C:44]([Cl:45])=[CH:43][N:42]=[CH:41][C:40]=2[Cl:46])[CH2:16][CH2:15][CH2:14][CH2:13]1>CO>[CH:12]1([O:17][C:18]2[C:19]([O:47][CH3:48])=[CH:20][CH:21]=[C:22]3[C:27]=2[N:26]([CH2:28][CH2:29][OH:30])[C:25](=[O:37])[CH:24]=[C:23]3[NH:38][C:39]2[C:40]([Cl:46])=[CH:41][N:42]=[CH:43][C:44]=2[Cl:45])[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 66781834HCID 66781834, compound

Product 1

HCID 24851913HCID 24851913, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

p-Toluenesulfonic acid (172 mg, 1.0 mmol) was added to a solution of 8-(cyclopentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)quinolin-2(1H)-one (2.4 g, 4.4 mmol) and methanol (100 mL). After stirring overnight, the reaction was concentrated, diluted with dichloromethane (100 mL), and then washed with sat'd NaHCO3 (20 mL) followed by water (20 mL). The organic layer was dried, filtered, concentrated, and recrystallized from dichloromethane/petroleum ether (1:2) to give 8-(cyclopentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-1-(2-hydroxyethyl)-7-methoxyquinolin-2(1H)-one: 1H NMR (400 MHz, DMSO-d6): δ 8.74 (s, 2H), 8.73 (s, 1H), 7.91 (d, 1H), 7.11 (d, 1H), 4.92 (s, 1H), 4.65 (t, 2H), 4.59 (m, 1H), 4.50 (t, 1H), 3.90 (s, 3H), 3.32 (m 2H), 1.80-1.48 (m, 8H); MS (ESI): 463.9.

Workup

  1. concentrationthe reaction was concentrated
  2. additiondiluted with dichloromethane (100 mL)
  3. washwashed with sat'd NaHCO3 (20 mL)
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customrecrystallized from dichloromethane/petroleum ether (1:2)

Sources & evidence

ORD record
ord-24787fcc025149928da61f6c4a837921
Source dataset
uspto-grants-2012_09
Patent number
US08258154B2

Reaction notes

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