2-(Dimethylamino)ethanol → HCID 89782856, compound

HRID 877447Notes

Reaction equation

HRID 877447 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[N:21]([CH2:22][C:23]([OH:25])=[O:24])[N:20]=[C:19]([C:26]([F:29])([F:28])[F:27])[CH:18]=3)=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].[CH3:30][N:31]([CH3:35])[CH2:32][CH2:33]O.C(N(CC)CC)C>CS(C)=O.O>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[N:21]([CH2:22][C:23]([O:25][CH2:33][CH2:32][N:31]([CH3:35])[CH3:30])=[O:24])[N:20]=[C:19]([C:26]([F:29])([F:27])[F:28])[CH:18]=3)=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

6

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 8471TriethylamineHCID 89782773HCID 89782773, compound

Product 1

HCID 89782856HCID 89782856, compoundYield 6.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a stirred solution of compound 38 (0.2 g, 0.471 mmol), 2-(dimethylamino)ethanol (0.14 mL, 1.41 mmol) and triethylamine (0.126 mL, 0.942 mmol) in DMSO (5 mL) at RT was added Pybop (0.360 g, 0.706 mmol) and the reaction mixture stirred overnight. The reaction was then diluted with water (30 mL) and extracted with ethyl acetate (50 mL×3). The combined organic layer was washed with saturated brine, dried over sodium sulphate and concentrated. The crude reaction mixture was purified by column chromatography using 3% methanol in dichloromethane to afford 39 (15 mg, 6%). LCMS: 496.25 (M+1)+; 1H NMR (CD3OD, 400 MHz) δ 8.23 (s, 1H), 8.05 (d, 1H, J=8 Hz), 8.01 (d, 1H, J=7.6 Hz), 7.88 (d, 1H, J=8.4 Hz), 7.78 (t, 3H, J=8 Hz), 7.64 (d, 2H, J=8 Hz), 6.84 (s, 1H), 5.2 (s, 2H), 4.5 (t, 2H, J=4.8 Hz), 3.49 (d, 2H, J=4.8 Hz), 3.20 (s, 3H), 2.9 (s, 6H).

Workup

  1. extractionextracted with ethyl acetate (50 mL×3)
  2. washThe combined organic layer was washed with saturated brine
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated
  5. customThe crude reaction mixture
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-0d1a9e22f7be4efaadea5c886c203735
Source dataset
uspto-grants-2015_03
Patent number
US08987318B2

Reaction notes

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