Ethanolamine → HCID 9913037, compound

HRID 413955Notes

Reaction equation

HRID 413955 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C:13]([OH:15])=[O:14])=[N:4][N:3]1[CH2:16][C:17]1[S:18][C:19]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:20]=2[N:21]=1.[CH2:30]([CH2:32][NH2:33])[OH:31]>CC(C)=O>[CH2:30]([CH2:32][NH2:33])[OH:31].[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C:13]([OH:15])=[O:14])=[N:4][N:3]1[CH2:16][C:17]1[S:18][C:19]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:20]=2[N:21]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 1613Zopolrestat

Product 1

HCID 9913037HCID 9913037, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of [4-oxo-(5-trifluoromethyl-benzothiazol-2-ylmethyl)-3,4-dihydro-phthalazin-1-yl]-acetic acid (419 mg, 1.0 mmol) in acetone (20 mL) was added ethanolamine (611 mg, 10.0 mmol). After stirring at ambient temperature for 1.0 hour, the mixture was evaporated to a semi-solid, which was crystallized from ethanol:diethyl ether (1:4) to afford the title compound as a white crystalline solid (460 mg, 95%). mp: 119-121° C.; 1H NMR (D2O, 350 MHz): δ 3.30 (m, 2H), 3.66 (s, 2H), 3.79 (s, 6H), 5.47 (s, 2H), 7.19 (m, 1H), 7.48-7.71 (m, 5H), 7.99 (m, 1H).

Workup

  1. customthe mixture was evaporated to a semi-solid, which
  2. customwas crystallized from ethanol:diethyl ether (1:4)

Sources & evidence

ORD record
ord-273a601347c7498f90b856a6ed8ff7ee
Source dataset
uspto-grants-2003_05
Patent number
US06570013B2

Reaction notes

Loading…