Zopolrestat → HCID 12071529, compound

HRID 413957Notes

Reaction equation

HRID 413957 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.[N:30]([CH2:37][CH2:38][OH:39])([CH2:34][CH2:35][OH:36])[CH2:31][CH2:32][OH:33]>CC(C)=O>[N:30]([CH2:37][CH2:38][OH:39])([CH2:34][CH2:35][OH:36])[CH2:31][CH2:32][OH:33].[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 1613ZopolrestatHCID 7618Triethanolamine

Product 1

HCID 12071529HCID 12071529, compoundYield 86.9%

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 triethanolamine (1.49 g, 10.0 mmol). After stirring at ambient temperature for 1.0 hours, the mixture was evaporated to a semi-solid, which was crystallized from ethanol:acetone (1:4) to afford the title compound as a white crystalline solid (494 mg, 86%). mp: 83-84° C.; 1H NMR (D2O, 350 MHz): δ 3.30 (m, 6H), 3.67 (s, 2H), 3.79 (m, 6H), 5.47 (s, 2H), 7.17 (m, 1H), 7.48-7.71 (m, 5H), 8.01 (m, 1H); MS (Cl) 419 (MH).

Workup

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

Sources & evidence

ORD record
ord-4ba52b66eb2749b1a4af39d6f8e88f11
Source dataset
uspto-grants-2003_05
Patent number
US06570013B2

Reaction notes

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