Ethanolamine → HCID 178482541, compound

HRID 493705Notes

Reaction equation

HRID 493705 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([S:14]([CH2:17][CH2:18][C:19]([N:21]1[CH2:26][CH2:25][N:24]([CH2:27][C:28]3[N:29]([CH3:35])/[C:30](=[N:33]/[CH3:34])/[S:31][CH:32]=3)[CH2:23][CH:22]1[C:36](O)=[O:37])=[O:20])(=[O:16])=[O:15])[CH:8]=[CH:7]2.[CH2:39]([NH2:42])[CH2:40][OH:41].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(N(CC)CC)C>[Cl:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([S:14]([CH2:17][CH2:18][C:19]([N:21]1[CH2:26][CH2:25][N:24]([CH2:27][C:28]3[N:29]([CH3:35])/[C:30](=[N:33]/[CH3:34])/[S:31][CH:32]=3)[CH2:23][CH:22]1[C:36]([NH:42][CH2:39][CH2:40][OH:41])=[O:37])=[O:20])(=[O:16])=[O:15])[CH:8]=[CH:7]2

Participants

8

Reactant 5

HCID 700EthanolamineHCID 11430Potassium CarbonateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 178482542HCID 178482542, compound

Product 1

HCID 178482541HCID 178482541, compoundYield 55.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

1-(3-((6-Chloro-2-naphthyl)sulfonyl)propanoyl)-4-(((2Z)-3-methyl-2-(methylimino)-2,3-dihydro-1,3-thiazol-4-yl)methyl)piperazine-2-carboxylic acid dihydrochloride (0.4 g) obtained in Example 24 was dissolved in DMF (20 mL), and triethylamine (0.2 mL) was added thereto. With ice cooling, 2-ethanolamine (0.04 g), HOBt (0.12 g) and WSC (0.16 g) were added thereto, and the mixture was mixed at room temperature for 16 hours. The reaction solution was basified with an aqueous potassium carbonate solution, then extracted with chloroform, and the extract was dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified with a basic silica gel column to give the title compound (0.21 g) as a white powder.

Workup

  1. additionthe mixture was mixed at room temperature for 16 hours
  2. extractionextracted with chloroform
  3. dry with materialthe extract was dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was purified with a basic silica gel column

Sources & evidence

ORD record
ord-6ad64d60b05949ee892fbf76b8967208
Source dataset
uspto-grants-2009_05
Patent number
US07534887B2

Reaction notes

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