Ethyl 2-chloroethanecarboximidate hydrochloride → HCID 178449971, compound

HRID 1433179Notes

Reaction equation

HRID 1433179 reaction equation
[C:1]([NH:5][S:6]([C:9]1[C:10]([C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[C:17]([NH2:22])[CH:16]=2)=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C(O[C:27](=N)[CH2:28][Cl:29])C>C(O)C>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]2[NH:21][C:27]([CH2:28][Cl:29])=[N:22][C:17]=2[CH:16]=1)(=[O:8])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 12470659Ethyl 2-chloroethanecarboximidate hydrochlorideHCID 579349643',4'-Diamino-biphenyl-2-sulfonic acid tert-butylamide

Product 1

HCID 178449971HCID 178449971, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3′,4′-diamino-biphenyl-2-sulfonic acid tert-butylamide (1.0 g, 3.13 mmol), 2-chloroacetimidic acid ethyl ester hydrochloride salt (591 mg, 3.76 mmol) (prepared according to the procedure described in J. Med. Chem., 1986, 29, 2280) in anhydrous ethanol (100%, 20 mL) was stirred at room temperature for 4 h. The reaction mixture was concentrated under reduced pressure and extracted with ethyl acetate and brine. The organic layer was dried over Na2SO4, filtered, and the filtrate was concentrated in vacuo. The residue was purified by chromatography (silica, EtOAc) to afford the title compound as an off-white solid (708 mg, 60% yield). 1H NMR (400 MHz, CD3OD) δ (ppm): 8.14 (dd, 1H, J=8.1 Hz, J=1.5 Hz), 7.79 (m, 1H), 7.74 (dd, 1H, J=8.5 Hz, J=1.1 Hz), 7.65 (td, 1H, J=7.5 Hz, J=1.6 Hz), 7.57 (td, 1H, J=7.8 Hz, J=1.6 Hz), 7.50 (dd, 1H, J=8.3 Hz, J=1.6 Hz), 7.39 (dd, 1H, J=7.3 Hz, J=1.2 Hz), 5.05 (s, 2H), 1.02 (s, 9H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C18H20ClN3O2S: 378.89 (M+H), Found 378.1.

Workup

  1. customprepared
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. extractionextracted with ethyl acetate and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe residue was purified by chromatography (silica, EtOAc)

Sources & evidence

ORD record
ord-4b8f14e65fd547ab9459ef146c649d1f
Source dataset
uspto-grants-2009_11
Patent number
US07612211B2

Reaction notes

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