2'-Trifluoromethanesulfonyl-biphenyl-3,4-diamine → HCID 178527296, compound

HRID 1433224Notes

Reaction equation

HRID 1433224 reaction equation
[F:1][C:2]([F:21])([F:20])[S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([NH2:19])[CH:13]=1)(=[O:5])=[O:4].Cl.C(O[C:26](=N)[CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=1)C>CCO>[F:21][C:2]([F:20])([F:1])[S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:17]=[CH:16][C:15]2[NH:18][C:26]([CH2:27][O:28][C:29]3[CH:34]=[CH:33][C:32]([C:35]([F:36])([F:37])[F:38])=[CH:31][CH:30]=3)=[N:19][C:14]=2[CH:13]=1)(=[O:4])=[O:5]

Participants

4

Reactant 2

HCID 579349912'-Trifluoromethanesulfonyl-biphenyl-3,4-diamineHCID 690421402-(4-Trifluoromethyl-phenoxy)-acetimidic acid ethyl ester hydrochloride

Product 1

HCID 178527296HCID 178527296, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2′-trifluoromethanesulfonyl-biphenyl-3,4-diamine (0.042 g, 0.133 mmol) and 2-(4-trifluoromethyl-phenoxy)-acetimidic acid ethyl ester hydrochloride (0.045 g, 0.159 mmol, Example 1.1) in EtOH (4 mL) was stirred at room temperature for 12 hours. The reaction was concentrated to give a residue, which was purified by chromatography (silica, hexanes: EtOAc, 1:2) to afford the product as brown oil (0.065 g, 98%). 1H NMR (400 MHz, CD3OD) δ (ppm): 8.25 (d, 1H, J=7.6 Hz), 7.92 (td, 1H, J=8.4 Hz, J=1.6 Hz), 7.77 (td, 1H, J=8.4 Hz, J=1.2 Hz), 7.65-7.54 (m, 3H), 7.27-7.20 (m, 4H), 7.14 (d, 1H, J=8.4 Hz), 5.45 (s, 2H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C22H15F6N2O3S: 501.4 (M+H), Found 501.2.

Workup

  1. concentrationThe reaction was concentrated
  2. customto give a residue, which
  3. customwas purified by chromatography (silica, hexanes: EtOAc, 1:2)

Sources & evidence

ORD record
ord-dd9aa48da3004f59b8f3a52ade331e36
Source dataset
uspto-grants-2009_11
Patent number
US07612211B2

Reaction notes

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