1,4-Dioxane → 1-(6-Fluoro-4-(5-methyl-1,3,4-oxadiazol-2-yl)-3-(pyridin-2-yl)-quinolin-2-yl)ethanamine

HRID 1616066Notes

Reaction equation

HRID 1616066 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH:12]([NH:14]C(=O)OC(C)(C)C)[CH3:13])[C:6]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)=[C:5]2[C:28]1[O:29][C:30]([CH3:33])=[N:31][N:32]=1.O1CCOCC1>C(Cl)Cl.Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH:12]([NH2:14])[CH3:13])[C:6]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)=[C:5]2[C:28]1[O:29][C:30]([CH3:33])=[N:31][N:32]=1

Participants

5

Reactant 2

HCID 312751,4-DioxaneHCID 67595696Tert-butyl 1-(6-fluoro-4-(5-methyl-1,3,4-oxadiazol-2-yl)-3-(pyridin-2-yl)quinolin-2-yl)ethylcarbamate

Product 1

HCID 696756651-(6-Fluoro-4-(5-methyl-1,3,4-oxadiazol-2-yl)-3-(pyridin-2-yl)-quinolin-2-yl)ethanamine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 1-(6-fluoro-4-(5-methyl-1,3,4-oxadiazol-2-yl)-3-(pyridin-2-yl)quinolin-2-yl)ethylcarbamate (0.252 g, 0.561 mmol) in DCM (1.121 mL) and hydrochloric acid, 4M solution in 1,4-dioxane (2.80 mL, 11.21 mmol) was stirred at rt. After 24 h, the mixture was partitioned between DCM (50 mL) and water (50 mL). The acidic aq mixture was washed with DCM (30 mL×2) to remove organic impurities. The aq layer was basified to ˜pH 13 with 10N NaOH (1 mL) and extracted with DCM (50 mL×3). The combined organic layers were washed with water (100 mL×1), dried over MgSO4, filtered, and concentrated in vacuo to give 1-(6-fluoro-4-(5-methyl-1,3,4-oxadiazol-2-yl)-3-(pyridin-2-yl)-quinolin-2-yl)ethanamine as an off-white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.60-8.65 (1H, m), 8.24-8.31 (1H, m), 7.80-7.91 (3H, m), 7.41-7.49 (2H, m), 4.03 (1H, q, J=6.6 Hz), 2.34 (3H, s), 2.03 (2H, br. s.), 1.24 (3H, d, J=6.7 Hz); LC-MS (ESI) m/z 350.0 [M+H]+. The solid was carried on crude without further purification.

Workup

  1. customthe mixture was partitioned between DCM (50 mL) and water (50 mL)
  2. washThe acidic aq mixture was washed with DCM (30 mL×2)
  3. customto remove organic impurities
  4. extractionextracted with DCM (50 mL×3)
  5. washThe combined organic layers were washed with water (100 mL×1)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ea5809df7a994e45a3b4d5209163f26c
Source dataset
uspto-grants-2014_07
Patent number
US08765768B2

Reaction notes

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