Trifluoroacetic acid → Diethyl(4-(2-amino-5-(thiophen-2-yl)phenylcarbamoyl)benzylamino)methylphosphonate

HRID 1013537Notes

Reaction equation

HRID 1013537 reaction equation
CC(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)=[CH:11][C:10]=1[NH:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([CH2:29][NH:30][CH2:31][P:32](=[O:39])([O:36][CH2:37][CH3:38])[O:33][CH2:34][CH3:35])=[CH:25][CH:24]=1)=[O:22])=O)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)=[CH:11][C:10]=1[NH:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([CH2:29][NH:30][CH2:31][P:32](=[O:39])([O:36][CH2:37][CH3:38])[O:33][CH2:34][CH3:35])=[CH:25][CH:24]=1)=[O:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57925892Diethyl [({[4-({[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-5-(2-thienyl)phenyl]amino}carbonyl)phenyl]methyl}amino)methyl)phosphonate

Product 1

HCID 42601485Diethyl(4-(2-amino-5-(thiophen-2-yl)phenylcarbamoyl)benzylamino)methylphosphonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

diethyl [({[4-({[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-5-(2-thienyl)phenyl]amino}carbonyl)phenyl]methyl}amino)methyl]phosphonate (360 mg, 0.628 mmol) was taken up in DCM (6 mL)/TFA (2 mL). After 4 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 Na2SO4 and concentrated in vacuo to give diethyl [({[4-({[2-amino-5-(2-thienyl)phenyl]amino) carbonyl}phenyl]methyl}amino)methyl]phosphonate as a beige solid. 1H NMR (DMSO-d6, 600 MHz) δ 9.67 (s, 1H), 7.93 (d, J=8.4 Hz, 2H), 7.43 (m, 3H), 7.32 (dd, J=4.8 and 0.6 Hz, 1H), 7.26 (dd, J=8.4 and 1.8 Hz, 1H), 7.21 (m, 1H), 7.01 (dd, J=5.4 and 3.6 Hz, 1H), 6.78 (d, J=8.4 Hz, 1H), 5.12 (s, 2H), 3.99 (m, 4H), 3.81 (s, 2H), 2.81 (d, J=12.0 Hz, 2H), 2.40 (br s, 1H), 1.20 (t, J=7.2 Hz, 6H). MS: cal'd 474 (MH+), exp 474.

Workup

  1. customthe solvent was removed in vacuo, saturated NaHCO3
  2. additionwas added
  3. extractionthe products extracted into EtOAc (×2)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-05a84de71f9e4aa9ba5fcc86192e8112
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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