Trifluoroacetic acid → [4-({[2-Amino-5-(2-thienyl)phenyl]amino}carbonyl)phenyl]methyl dimethylphosphinate

HRID 1013519Notes

Reaction equation

HRID 1013519 reaction equation
[CH3:1][P:2]([CH3:34])(=[O:33])[O:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([NH:13][C:14]2[CH:19]=[C:18]([C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)[CH:17]=[CH:16][C:15]=2[NH:25]C(OC(C)(C)C)=O)=[O:12])=[CH:7][CH:6]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][P:2]([CH3:34])(=[O:33])[O:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([NH:13][C:14]2[CH:19]=[C:18]([C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)[CH:17]=[CH:16][C:15]=2[NH2:25])=[O:12])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57925914[4-({[2-({[(1,1-Dimethylethyl)oxy]carbonyl}amino)-5-(2-thienyl)phenyl]amino}carbonyl)phenyl]methyl dimethylphosphinate

Product 1

HCID 25013976[4-({[2-Amino-5-(2-thienyl)phenyl]amino}carbonyl)phenyl]methyl dimethylphosphinate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[4-({[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-5-(2-thienyl)phenyl]amino}carbonyl)phenyl]methyl dimethylphosphinate (1.1 g, 2.198 mmol) was taken up in DCM (20 mL)/TFA (8 mL). After 2 hours at room temperature the solvent was removed in vacuo. Saturated NaHCO3 was added and the products extracted into EtOAc (×2). The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was triturated in EtOAc to give [4-({[2-amino-5-(2-thienyl)phenyl]amino}carbonyl)phenyl]methyl dimethylphosphinate as a beige solid. 1H-NMR (600 mHz, DMSO-d6) δ 9.72 (s, 1H), 7.98 (d, J=8.4 Hz, 2H), 7.49 (d, J=8.4 Hz, 2H), 7.44 (d, J=1.8 Hz, 1H), 7.32 (dd, J=4.8 and 1.2 Hz, 1H), 7.27 (dd, J=8.4 and 2.4 Hz, 1H), 7.21 (dd, J=3.6 and 1.2 Hz, 1H), 7.01 (dd, J=4.8 and 3.6 Hz, 1H), 6.78 (d, J=8.4 Hz, 1H), 5.13 (s, 2H), 5.01 (d, J=8.4 Hz, 2H), 1.45 (d, J=14.4 Hz, 6H). MS: cal'd 401 (MH+), exp 401 (MH+).

Workup

  1. customAfter 2 hours at room temperature the solvent was removed in vacuo
  2. additionSaturated NaHCO3 was added
  3. extractionthe products extracted into EtOAc (×2)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated in EtOAc

Sources & evidence

ORD record
ord-234aa100e1f84ed4a8bf6df969eb31c6
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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