p-Toluenesulfonic acid → HCID 24851913, compound

HRID 1522813Notes

Reaction equation

HRID 1522813 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 stifling 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-59808fee21974c63a2e7b4dbdd64d961
Source dataset
uspto-grants-2015_07
Patent number
US09078887B2

Reaction notes

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