Potassium Carbonate → HCID 69654562, compound

HRID 1244006Notes

Reaction equation

HRID 1244006 reaction equation
Cl.Cl.[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[CH2:15][NH:16][C@H:17]1[CH2:22][CH2:21][CH2:20][NH:19][C@H:18]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[N:11]([CH3:29])[C:10](=[O:30])[CH2:9][CH2:8]2.C(=O)([O-])[O-].[K+].[K+].Cl[C:38]1[O:39][C:40]2[CH:46]=[CH:45][CH:44]=[CH:43][C:41]=2[N:42]=1>O1CCOCC1>[O:39]1[C:40]2[CH:46]=[CH:45][CH:44]=[CH:43][C:41]=2[N:42]=[C:38]1[N:19]1[CH2:20][CH2:21][CH2:22][C@H:17]([NH:16][CH2:15][C:14]2[CH:13]=[C:12]3[C:7]([CH2:8][CH2:9][C:10](=[O:30])[N:11]3[CH3:29])=[CH:6][C:5]=2[O:4][CH3:3])[C@@H:18]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 119862-ChlorobenzoxazoleHCID 69654767HCID 69654767, compound

Product 1

HCID 69654562HCID 69654562, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 6-Methoxy-1-methyl-7-[(2S,3S)-(2-phenyl-piperidin-3-ylamino)-methyl]-3,4-dihydro-1H-quinolin-2-one dihydrochloride (50 mg, 0.11 mmol), freshly ground potassium carbonate (61 mg, 0.44 mmol), and catalytic KI in 3 mL of 1,4-dioxane was added 2-chlorobenzoxazole (126 mg, 0.11 mmol). After heating at reflux for 5 days, the reaction was cooled and partitioned between ethyl acetate and water. The organic portion was separated, dried over MgSO4, filtered, and concentrated. Silica gel chromatography (99:1 chloroform/methanol followed by 3:1 ethyl acetate/hexane) gave 31 mg (56%) of the title compound as a light brown oil. MS (M+H)+=497.2; 1H NMR (400 MHz, CDCl3): δ 1.75–1.85 (m, 1H), 1.85–1.95 (m, 3H), 2.55–2.60 (t, J=7 Hz, 2H), 2.80–2.85 (t, J=7 Hz, 2H), 3.15–3.25 (m, 1H), 3.30 (s, 3H), 3.30–3.40 (t, J=13 Hz, 1H), 3.71 (s, 3H), 3.82–3.92 (q, J=13.5 Hz, 2H), 4.16–4.21 (dd, J=13 Hz, 3.8 Hz, 1H), 5.74–5.76 (d, J=5.6 Hz, 1H), 6.62 (s, 1H), 6.90 (s, 1H), 6.95–6.99 (t, J=8.5 Hz, 1H), 7.10–7.14 (t, J=8.5 Hz, 1H), 7.19–7.21 (d, J=7.9 Hz, 1H), 7.24–7.28 (m, 4H), 7.68–7.70 (d, J=7.5 Hz, 2H); 13C NMR (100 MHz, CDCl3): δ 24.2, 25.5, 26.8, 29.6, 31.7, 41.4, 46.0, 55.5, 56.9, 58.5, 108.5, 110.2, 116.0, 116.4, 120.3, 123.8, 125.7, 126.8, 127.5, 128.3, 129.3, 133.7, 137.7, 143.2, 148.5, 152.9, 162.3, 169.9. The dihydrochloride salt was prepared by the addition of 2 M HCl in ether to a solution of the product in ethyl acetate. Concentration gave a white solid (Mp=181–183° C.).

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 5 days
  3. temperaturethe reaction was cooled
  4. custompartitioned between ethyl acetate and water
  5. customThe organic portion was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5ff9d4fe17f94cfda8b3add3dd7e50dc
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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