5-Diethylaminomethyl-4-methyl-thiophene-2-carboxylic acid → N-(2-Amino-ethyl)-4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-benzenesulfonamide

HRID 1685761Notes

Reaction equation

HRID 1685761 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][NH:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([C:20](=[NH:23])[NH:21][OH:22])=[CH:16][CH:15]=1)(=[O:13])=[O:12])(C)(C)C.[CH2:25]([N:27]([CH2:30][C:31]1[S:35][C:34]([C:36](O)=O)=[CH:33][C:32]=1[CH3:39])[CH2:28][CH3:29])[CH3:26]>Cl.O1CCOCC1.O>[NH2:7][CH2:8][CH2:9][NH:10][S:11]([C:14]1[CH:15]=[CH:16][C:17]([C:20]2[N:23]=[C:36]([C:34]3[S:35][C:31]([CH2:30][N:27]([CH2:28][CH3:29])[CH2:25][CH3:26])=[C:32]([CH3:39])[CH:33]=3)[O:22][N:21]=2)=[CH:18][CH:19]=1)(=[O:12])=[O:13]

Participants

6

Reactant 2

HCID 672654805-Diethylaminomethyl-4-methyl-thiophene-2-carboxylic acidHCID 178453718HCID 178453718, compound

Product 1

HCID 67265224N-(2-Amino-ethyl)-4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-benzenesulfonamideYield 3.5%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Crude (2-{4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-benzenesulfonylamino}-ethyl)-carbamic acid tert-butyl ester (156 mg) is obtained starting from {2-[4-(N-hydroxycarbamimidoyl)-benzenesulfonylamino]-ethyl}-carbamic acid tert-butyl ester (277 mg, 0.774 mmol) and 5-diethylaminomethyl-4-methyl-thiophene-2-carboxylic acid (160 mg, 0.704 mmol) according to Method A; LC-MS: tR=0.61 min; [M+1]+=550.16. This material (156 mg, 0.284 mmol) is dissolved in 4 M HCl in dioxane (5 mL) and the mixture is stirred at rt for 18 h. The mixture is diluted with water and washed with EA. The organic washing is extracted with water. The combined aq. extracts are neutralised by adding sat. aq. NaHCO3 solution and extracted twice with EA. These organic extracts are combined, dried over MgSO4, filtered and concentrated. The crude product is purified by prep. HPLC (XBridge, eluting with a gradient of acetonitrile in water containing 0.5% of aq. ammonia) to give the title compound (11 mg) as a pale yellow oil; LC-MS: tR=0.42 min; [M+1]+=449.64.

Workup

  1. washwashed with EA
  2. washThe organic washing
  3. extractionis extracted with water
  4. additionby adding sat. aq. NaHCO3 solution
  5. extractionextracted twice with EA
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product is purified by prep
  10. washHPLC (XBridge, eluting with a gradient of acetonitrile in water containing 0.5% of aq. ammonia)

Sources & evidence

ORD record
ord-a07fc819e92c4c53a76a5f4d39f85074
Source dataset
uspto-grants-2012_04
Patent number
US08148410B2

Reaction notes

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