HCID 58229494, compound → HCID 58229504, compound

HRID 1963791Notes

Reaction equation

HRID 1963791 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:6][C:5]([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]=[CH:18][CH:17]=[C:16]3[C:23]2[CH2:24][CH2:25][O:26][CH2:27][CH:28]=2)=[CH:4][N:3]=1>[Pt](=O)=O>[Cl:1][C:2]1[C:7]([NH:8][S:9]([CH3:12])(=[O:10])=[O:11])=[CH:6][C:5]([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]=[CH:18][CH:17]=[C:16]3[CH:23]2[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)=[CH:4][N:3]=1

Participants

3

Reactant 1

HCID 58229494HCID 58229494, compound

Product 1

HCID 58229504HCID 58229504, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 345198Adams' catalystCatalyst

Procedure

To a solution of N-(2-chloro-5-(4-(3,6-dihydro-2H-pyran-4-yl)quinolin-6-yl)pyridin-3-yl)methanesulfonamide (0.055 g, 0.13 mmol) in (10 mL) under N2 was added platinum (IV) oxide (0.015 g, 0.066 mmol). The reaction mixture was purged with N2 followed by evacuating. This procedure was done 3 times. After last evacuation, a hydrogen balloon was inserted. The reaction was stirred at rt under H2 for 4 h. The reaction mixture was passed through a pad of Celite® (diatomaceous earth). The reaction mixture was then concentrated. The crude product was purified by column chromatography (12 g, 20% to 30% acetone in hexanes) to afford the desired product as an off-white solid (30.0 mg). MS (ESI pos. ion) m/z: calcd for C20H26ClN3O3S: 417.1; found: 417.9 [M+1]. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.85-2.14 (m, 4 H) 3.14 (s, 3 H) 3.55-3.85 (m, 3 H) 4.10-4.29 (m, 2 H) 6.93 (br. s., 1 H) 7.39 (d, J=4.53 Hz, 1 H) 7.92 (dd, J=8.70, 1.97 Hz, 1 H) 8.17-8.37 (m, 3 H) 8.57 (d, J=2.34 Hz, 1 H) 8.94 (d, J=4.53 Hz, 1 H).

Workup

  1. customThe reaction mixture was purged with N2
  2. customby evacuating
  3. concentrationThe reaction mixture was then concentrated
  4. customThe crude product was purified by column chromatography (12 g, 20% to 30% acetone in hexanes)

Sources & evidence

ORD record
ord-9db7fe4486f140489749cbca1acdbad2
Source dataset
uspto-grants-2013_04
Patent number
US08415376B2

Reaction notes

Loading…