2-(Dimethylamino)ethanol → HCID 57968934, compound

HRID 1255661Notes

Reaction equation

HRID 1255661 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 silica 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 silica gel
  3. washeluting with 5% MeOH/DCM

Sources & evidence

ORD record
ord-82456e271a134321910c9dda425ae122
Source dataset
uspto-grants-2013_06
Patent number
US08461135B2

Reaction notes

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