p-Toluenesulfonic acid → HCID 24851913, compound

HRID 659064Notes

Reaction equation

HRID 659064 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-cded98346941423fa0b332b168757e66
Source dataset
uspto-grants-2011_12
Patent number
US08080563B2

Reaction notes

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