Dimethylamine → HCID 25254371, compound

HRID 219477Notes

Reaction equation

HRID 219477 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[C:10]([O:11][CH2:12][CH2:13][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH3:15])=[C:9]([O:23][CH3:24])[C:8]([Cl:25])=[C:7]([CH3:26])[C:6]=1[C:27](=[O:29])[CH3:28].[CH3:30][NH:31][CH3:32].C1COCC1>>[Cl:25][C:8]1[C:7]([CH3:26])=[C:6]([C:27](=[O:29])[CH3:28])[C:5]([O:4][CH2:3][CH2:2][N:31]([CH3:32])[CH3:30])=[C:10]([O:11][CH2:12][CH2:13][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH3:15])[C:9]=1[O:23][CH3:24]

Participants

4

Reactant 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 595835231-{2-(2-Bromo-ethoxy)-5-chloro-3-[3-(4-fluoro-phenyl)-butoxy]-4-methoxy-6-methyl-phenyl}-ethanone

Product 1

HCID 25254371HCID 25254371, compoundYield 56%

Procedure

Example 8a (50 mg, 0.10 mmol) was reacted with 1.0 M solution of dimethylamine in THF (1 mL, 1 mmol) at 55° C. at for 24 h. The solvent was removed under vacuum and the crude mixture was suspended in Et2O (910 mL) and 2N HCl (10 mL). The ethereal layer was separated, dried over MgSO4 and evaporated to dryness. The isolated white solid was again suspended in mixture of Et2O and hexane (1/9) sonicated for 1 minute and solid was filtered and dried. The isolated solid was suspended in DCM and washed with NaHCO3 (aq) solution. The organic layer was dried over MgSO4 and evaporated to dryness to afford the title compound as a pale yellow oil (26 mg, 56%). 1H NMR (300 MHz, CDCl3) δ 7.20-7.15 (m, 2H), 7.00-6.95 (m, 2H), 4.05 (t, J=6.0 Hz, 2H), 3.96 (t, J=6.6 Hz, 2H), 3.82 (s, 3H), 3.03-2.96 (m, 1H), 2.57 (t, J=6.0 Hz, 2H), 2.49 (s, 3H), 2.27 (s, 6H), 2.18 (s, 3H), 2.03-1.98 (m, 2H), 1.29 (d, J=6.9 Hz, 3H). MS (ES+) m/z 452.2.2 (M+H+).

Workup

  1. customThe solvent was removed under vacuum
  2. customThe ethereal layer was separated
  3. dry with materialdried over MgSO4
  4. customevaporated to dryness
  5. additionThe isolated white solid was again suspended in mixture of Et2O and hexane (1/9)
  6. customsonicated for 1 minute
  7. filtrationsolid was filtered
  8. customdried
  9. washwashed with NaHCO3 (aq) solution
  10. dry with materialThe organic layer was dried over MgSO4
  11. customevaporated to dryness

Sources & evidence

ORD record
ord-0385b2b1a518439090b1b28922a2e36b
Source dataset
uspto-grants-2012_06
Patent number
US08202513B2

Reaction notes

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