Citric Acid → N-[2-(diethylamino)ethyl]-N-(2-{[2-(4-hydroxy-2-oxo-2,3-dihydro-1,3-benzothiazol-7-yl)ethyl]amino}ethyl)-3-[2-(1-naphthyl)ethoxy]propanamide citrate

HRID 556721Notes

Reaction equation

HRID 556721 reaction equation
[C:1]([OH:13])(=[O:12])[CH2:2][C:3]([CH2:8][C:9]([OH:11])=[O:10])([C:5]([OH:7])=[O:6])[OH:4].[CH2:14]([N:16]([CH2:53][CH3:54])[CH2:17][CH2:18][N:19]([CH2:37][CH2:38][NH:39][CH2:40][CH2:41][C:42]1[C:50]2[S:49][C:48](=[O:51])[NH:47][C:46]=2[C:45]([OH:52])=[CH:44][CH:43]=1)[C:20](=[O:36])[CH2:21][CH2:22][O:23][CH2:24][CH2:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][CH:27]=1)[CH3:15]>CO>[C:1]([OH:13])(=[O:12])[CH2:2][C:3]([CH2:8][C:9]([OH:11])=[O:10])([C:5]([OH:7])=[O:6])[OH:4].[CH2:53]([N:16]([CH2:14][CH3:15])[CH2:17][CH2:18][N:19]([CH2:37][CH2:38][NH:39][CH2:40][CH2:41][C:42]1[C:50]2[S:49][C:48](=[O:51])[NH:47][C:46]=2[C:45]([OH:52])=[CH:44][CH:43]=1)[C:20](=[O:36])[CH2:21][CH2:22][O:23][CH2:24][CH2:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][CH:27]=1)[CH3:54]

Participants

4

Reactant 2

HCID 311Citric AcidHCID 16035068Azd-3199

Product 1

HCID 66992113N-[2-(diethylamino)ethyl]-N-(2-{[2-(4-hydroxy-2-oxo-2,3-dihydro-1,3-benzothiazol-7-yl)ethyl]amino}ethyl)-3-[2-(1-naphthyl)ethoxy]propanamide citrateYield 45%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Citric Acid (248.96 mg) was added to a solution of N-[2-(diethylamino)ethyl]-N-(2-{[2-(4-hydroxy-2-oxo-2,3-dihydro-1,3-benzothiazol-7-yl)ethyl]amino}ethyl)-3-[2-(1-naphthyl)ethoxy]propanamide (0.5 g) in methanol (5 mL). Immediately, the clear solution became opaque and orange oil settled out. This mixture was heated at an external temp of 60° C. forming a clear solution, which was then allowed to cool to room temperature and stirred for 48 h. The resulting precipitate was collected by filtration and washed with methanol (1 mL) and diethyl ether (1 mL). The solid was then dried in vacuo at room temperature for 4 h to give the title compound (0.3 g).

Workup

  1. customforming a clear solution, which
  2. temperatureto cool to room temperature
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with methanol (1 mL) and diethyl ether (1 mL)
  5. customThe solid was then dried in vacuo at room temperature for 4 h

Sources & evidence

ORD record
ord-01dd431abb1747cdb77976fb9052e323
Source dataset
uspto-grants-2011_11
Patent number
US08058294B2

Reaction notes

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