Diisopropylethylamine → HCID 86599660, compound

HRID 1784186Notes

Reaction equation

HRID 1784186 reaction equation
[CH3:1][C:2]1[C:3]([CH:8]2[CH2:13][C:12]([CH3:15])([OH:14])[CH2:11][CH:10]([C:16]3[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][N:17]=3)[NH:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.Br[CH2:24][CH2:25][CH2:26][CH2:27][N:28]1[C:36](=[O:37])[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]1=[O:38].CCN(C(C)C)C(C)C>CN(C=O)C>[OH:14][C:12]1([CH3:15])[CH2:13][CH:8]([C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]=2)[N:9]([CH2:24][CH2:25][CH2:26][CH2:27][N:28]2[C:36](=[O:37])[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:29]2=[O:38])[CH:10]([C:16]2[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][N:17]=2)[CH2:11]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 93575N-(4-Bromobutyl)phthalimideHCID 86599661HCID 86599661, compound

Product 1

HCID 86599660HCID 86599660, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of meso-2′β,6′β-[3,4′,3″-trimethyl-1′,2′,3′,4′,5′,6′-hexahydro-[2,2′;6′,2″]terpyridin-4′-ol (0.2499 g, 0.84 mmol) in DMF (9 mL) was added 2-(4-bromo-butyl)-isoindole-1,3-dione (0.2605 g, 0.92 mmol), KI (0.0142 g, 0.08 mmol), and DIPEA (0.29 mL, 1.68 mmol), and stirred at 60° C. for 24 hours. The mixture was concentrated, and saturated NaHCO3 (30 mL) was added and extracted with CH2Cl2 (3×35 mL). The combined organic extracts were washed with brine (2×20 mL), dried (Na2SO4), filtered, and concentrated. Purification of the crude material by column chromatography on silica gel (50:1:1 CH2Cl2—MeOH—NH4OH) provided 0.3144 g (75%) of meso-2′β,6′β-[2-[4-(4′-hydroxy-3,4′,3″-trimethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridin-1′yl)-butyl]-isoindole-1,3-dione as a white solid. 1H NMR (CDCl3) δ 0.48 (s, 1H), 0.86 (s, 2H), 1.42 (s, 3H), 1.68-1.72 (m, 2H), 2.18-2.38 (m, 6H), 2.45 (s, 6H), 3.15 (t, 2H, J=6.0 Hz), 4.13 (d, 2H, J=12.0 Hz), 6.94-7.03 (m, 2H), 7.25-7.34 (m, 2H), 7.67-7.70 (m, 2H), 7.75-7.78 (m, 2H), 8.32-8.34 (m, 2H).

Workup

  1. concentrationThe mixture was concentrated
  2. additionsaturated NaHCO3 (30 mL) was added
  3. extractionextracted with CH2Cl2 (3×35 mL)
  4. washThe combined organic extracts were washed with brine (2×20 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification of the crude material by column chromatography on silica gel (50:1:1 CH2Cl2—MeOH—NH4OH)

Sources & evidence

ORD record
ord-3f169f4154fd4ae78f611376589451ea
Source dataset
uspto-grants-2009_03
Patent number
US07501518B2

Reaction notes

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