2-(Dimethylamino)ethanol → HCID 57968934, compound

HRID 1471519Notes

Reaction equation

HRID 1471519 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[CH:8][C:9]([O:11][C:12]3[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=3)=[CH:10][C:5]=2[CH2:4][O:3]1.[CH3:21][N:22]([CH2:24][CH2:25]O)[CH3:23].CCN=C=NCCCN(C)C>CN(C=O)C>[CH3:21][N:22]([CH3:23])[CH2:24][CH2:25][O:17][C:16](=[O:18])[C:15]1[CH:14]=[CH:13][C:12]([O:11][C:9]2[CH:8]=[CH:7][C:6]3[B:2]([OH:1])[O:3][CH2:4][C:5]=3[CH:10]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25010450Benzoic acid, 4-[(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-5-yl)oxy]-

Product 1

HCID 57968934HCID 57968934, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a clear solution of 4-(1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-5-yloxy)-benzoic acid ((C38), 0.5 g, 1.75 mmol) in DMF (20 mL) were added N,N-dimethylamino ethanol (0.37 mL, 3.7 mmol) and EDCI (0.71 g, 3.7 mmol). The reaction was stirred at room temperature overnight. Then DMF was evaporated under vacuum. The residue was purified over sililca gel, eluting with 5% MeOH/DCM, to afford the 0.35 g of the title compound in 56% yield. 1H NMR 400 MHz (DMSO-d6) δ: 7.97 (d, J=8.9 Hz, 2H), 7.76 (d, J=7.8 Hz, 1H), 7.15-7.07 (m, 4H), 4.95 (s, 2H), 4.33 (t, J=5.5 Hz, 2H), 2.58 (t, J=5.9 Hz, 2H), 2.20 (s, 6H); MS (ES) m/z: 342 (M+H)'; HPLC purity: 91.90% (220 nm), 94.99% (254 nm).

Workup

  1. customThen DMF was evaporated under vacuum
  2. customThe residue was purified over sililca gel
  3. washeluting with 5% MeOH/DCM

Sources & evidence

ORD record
ord-c391c6aeb5ae4b91bedb7ada653716a2
Source dataset
uspto-grants-2015_04
Patent number
US09012431B2

Reaction notes

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