Benzoic 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 mono benzoate

HRID 556723Notes

Reaction equation

HRID 556723 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10]([N:12]([CH2:49][CH3:50])[CH2:13][CH2:14][N:15]([CH2:33][CH2:34][NH:35][CH2:36][CH2:37][C:38]1[C:46]2[S:45][C:44](=[O:47])[NH:43][C:42]=2[C:41]([OH:48])=[CH:40][CH:39]=1)[C:16](=[O:32])[CH2:17][CH2:18][O:19][CH2:20][CH2:21][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1)[CH3:11]>CO>[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:49]([N:12]([CH2:10][CH3:11])[CH2:13][CH2:14][N:15]([CH2:33][CH2:34][NH:35][CH2:36][CH2:37][C:38]1[C:46]2[S:45][C:44](=[O:47])[NH:43][C:42]=2[C:41]([OH:48])=[CH:40][CH:39]=1)[C:16](=[O:32])[CH2:17][CH2:18][O:19][CH2:20][CH2:21][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1)[CH3:50]

Participants

4

Reactant 2

HCID 243Benzoic AcidHCID 16035068Azd-3199

Product 1

HCID 25155911N-[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 mono benzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Benzoic acid (52.75 mg) was added in one portion 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 (0.25 g) in methanol (2.5 mL) producing a clear solution. This was stirred at room temperature for 1 h then the solvent was removed in vacuo. The residue was stirred in acetonitrile (5 mL) at room temperature for 16 h then the solvent was removed and methyl t-butyl ether (10 mL) was added. This mixture was stirred at room temperature for 3 h before the title compound was collected by filtration. The title compound was isolated as an amorphous solid.

Workup

  1. customproducing a clear solution
  2. customthe solvent was removed in vacuo
  3. stirringThe residue was stirred in acetonitrile (5 mL) at room temperature for 16 h
  4. customthe solvent was removed
  5. additionmethyl t-butyl ether (10 mL) was added
  6. stirringThis mixture was stirred at room temperature for 3 h before the title compound
  7. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-03342b1240ea4865952d3a9193d1ecba
Source dataset
uspto-grants-2011_11
Patent number
US08058294B2

Reaction notes

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