Hydrochloric Acid → HCID 59842996, compound

HRID 1878733Notes

Reaction equation

HRID 1878733 reaction equation
F[C:2]1[C:7]([CH2:8][CH2:9][O:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=3)[N:14]=[CH:13][CH:12]=2)=[CH:6][C:5]([C:23]2[S:24][CH:25]=[C:26]([CH3:28])[CH:27]=2)=[CH:4][N:3]=1.Cl.[O:30]1CCOCC1>>[CH3:22][O:21][C:17]1[CH:16]=[C:15]2[C:20]([C:11]([O:10][CH2:9][CH2:8][C:7]3[C:2](=[O:30])[NH:3][CH:4]=[C:5]([C:23]4[S:24][CH:25]=[C:26]([CH3:28])[CH:27]=4)[CH:6]=3)=[CH:12][CH:13]=[N:14]2)=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59843028HCID 59843028, compound

Product 1

HCID 59842996HCID 59842996, compound

Conditions

Temperature
105 °C

Procedure

To a 4 mL microwave tube was added 4-(2-(2-fluoro-5-(4-methylthiophen-2-yl)pyridin-3-yl)ethoxy)-7-methoxyquinoline (0.025 g, 0.063 mmol), aq. HCl (5N, 2 mL), and dioxane (3 mL). The resulting mixture was sealed and heated to reflux (105° C.) in closed system for 20 h. The reaction mixture was partitioned between EtOAc/satd. NaHCO3. The aqueous layer was extracted with EtOAc and the combined organic layers were dried over MgSO4 and concentrated. The crude product was purified using SiO2 chromatography with CH2Cl2:EtOAc:MeOH (2M NH3) (90%:6%:4%) to afford the product as whit solid (15 mg). MS (ESI pos. ion) m/z (MH+): 393.3. Calc'd exact mass for C22H20N2O3S: 392.1. 1H NMR (300 MHz, MeOH-d4) δ ppm 2.24 (s, 3 H) 3.20 (t, J=6.28 Hz, 2 H) 3.93 (s, 3 H) 4.54 (t, J=6.28 Hz, 2 H) 6.90 (s, 1 H) 6.94 (d, J=5.55 Hz, 1 H) 6.96 (s, 1 H) 7.11 (dd, J=9.21, 2.48 Hz, 1 H) 7.27 (d, J=2.34 Hz, 1 H) 7.55 (d, J=2.63 Hz, 1 H) 7.88 (d, J=2.48 Hz, 1 H) 8.10 (d, J=9.21 Hz, 1 H) 8.57 (d, J=5.55 Hz, 1 H).

Workup

  1. customThe resulting mixture was sealed
  2. temperatureheated
  3. customThe reaction mixture was partitioned between EtOAc/
  4. extractionThe aqueous layer was extracted with EtOAc
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. concentrationconcentrated
  7. customThe crude product was purified

Sources & evidence

ORD record
ord-29ac5353234241679514bd7bae2ccca0
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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