Dimethylethylamine → HCID 67001735, compound

HRID 2279233Notes

Reaction equation

HRID 2279233 reaction equation
CN(C)CC.[CH:6]1([C:10]([N:12]2[CH2:18][CH2:17][CH:16]3[CH2:19][N:20]([CH2:23][C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)[CH2:21][CH2:22][N:15]3[C:14]3[N:31]=[CH:32][CH:33]=[CH:34][C:13]2=3)=O)[CH2:9][CH2:8][CH2:7]1>O1CCCC1>[CH:6]1([CH2:10][N:12]2[CH2:18][CH2:17][CH:16]3[CH2:19][N:20]([CH2:23][C:24]4[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=4)[CH2:21][CH2:22][N:15]3[C:14]3[N:31]=[CH:32][CH:33]=[CH:34][C:13]2=3)[CH2:9][CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 11723DimethylethylamineHCID 67001524HCID 67001524, compound

Product 1

HCID 67001735HCID 67001735, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of alane-dimethylethylamine complex (0.5 M in toluene, 3.1 mL, 1.55 mmol) was added to a stirring solution of the product of Example 65A (122 mg, 0.31 mmol) in tetrahydrofuran (5.0 mL) at room temperature under nitrogen. The turbid solution was stirred at room temperature for 4 hours. The reaction was quenched by addition of methanol (1 mL), followed after 5 minutes by water (5 mL) and 25% NaOH (0.5 mL). The aqueous layer was separated and extracted with ethyl acetate (2×5 mL) and the combined organic phase was washed with brine (5 mL), dried (Na2SO4) and concentrated under vacuum to provide a residue that was purified by preparative HPLC on a Phenomenex® Luna® C8(2) 5 μm 100 Å AXIA column (30×75 mm), eluted with methanol:10 mM (NH4)2CO3 in water (50:50-95:5) to provide the title compound 1H NMR (300 MHz, CDCl3) δ ppm 1.62-1.94 (m, 6H), 1.97-2.12 (m, 2H), 2.13-2.26 (m, 1H), 2.30-2.49 (m, 1H), 2.51-2.69 (m, 2H), 2.72-2.87 (m, 1H), 2.91-3.03 (m, 1H), 3.02-3.15 (m, 2H), 3.17-3.70 (m, 6H), 6.74 (dd, J=7.8, 4.7 Hz, 1H), 6.92 (dd, J=7.8, 1.4 Hz, 1H), 7.01 (t, J=8.6 Hz, 2H), 7.27-7.39 (m, 2H), 7.79 (dd, J=4.7, 1.7 Hz, 1H); MS (DCI) m/z 381 (M+H)+.

Workup

  1. customThe reaction was quenched by addition of methanol (1 mL)
  2. waitfollowed after 5 minutes by water (5 mL) and 25% NaOH (0.5 mL)
  3. customThe aqueous layer was separated
  4. extractionextracted with ethyl acetate (2×5 mL)
  5. washthe combined organic phase was washed with brine (5 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under vacuum
  8. customto provide a residue that
  9. customwas purified by preparative HPLC on a Phenomenex® Luna® C8(2) 5 μm 100 Å AXIA column (30×75 mm)
  10. washeluted with methanol

Sources & evidence

ORD record
ord-18a82548d5894a9381f4615fbea347d8
Source dataset
uspto-grants-2015_09
Patent number
US09133206B2

Reaction notes

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