Trifluoroacetic acid → N-[2-amino-5-(3-thienyl)-phenyl]-4-[2-anilino-1-({[(methylamino)carbonyl]amino}methyl)-2-oxoethyl]benzamide

HRID 1919913Notes

Reaction equation

HRID 1919913 reaction equation
[NH:1]([C:8](=[O:44])[CH:9]([C:16]1[CH:43]=[CH:42][C:19]([C:20]([NH:22][C:23]2[CH:28]=[C:27]([C:29]3[CH:33]=[CH:32][S:31][CH:30]=3)[CH:26]=[CH:25][C:24]=2[NH:34]C(=O)OC(C)(C)C)=[O:21])=[CH:18][CH:17]=1)[CH2:10][NH:11][C:12]([NH:14][CH3:15])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl.CCOC(C)=O>[NH2:34][C:24]1[CH:25]=[CH:26][C:27]([C:29]2[CH:33]=[CH:32][S:31][CH:30]=2)=[CH:28][C:23]=1[NH:22][C:20](=[O:21])[C:19]1[CH:18]=[CH:17][C:16]([CH:9]([CH2:10][NH:11][C:12]([NH:14][CH3:15])=[O:13])[C:8]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:44])=[CH:43][CH:42]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 57611898tert-Butyl [2-({4-[2-anilino-1-({[(methylamino)carbonyl]amino}methyl)-2-oxoethyl]-benzoyl}amino)-4-(3-thienyl)phenyl]carbamate

Product 1

HCID 24753765N-[2-amino-5-(3-thienyl)-phenyl]-4-[2-anilino-1-({[(methylamino)carbonyl]amino}methyl)-2-oxoethyl]benzamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl [2-({4-[2-anilino-1-({[(methylamino)-carbonyl]-amino}methyl)-2-oxoethyl]benzoyl}amino)-4-(3-thienyl)phenyl]carbamate (49 mg, 0.08 mmol) in CH2Cl2 (4 mL) was added trifluoroacetic acid (1 mL), and the reaction was stirred at room temperature for 3 h. Concentration yielded a yellow residue that was dissolved in EtOAc, neutralized with sat. NaHCO3, washed with brine, dried (MgSO4), and evaporated to give N-[2-amino-5-(3-thienyl)-phenyl]-4-[2-anilino-1-({[(methylamino)carbonyl]amino}methyl)-2-oxoethyl]benzamide as a white solid. 1H NMR (DMSO-d6) δ 10.19 (s, 1H), 9.66 (s, 1H), 7.95 (d, J=8.2 Hz, 2H), 7.58 (d, J=7.6 Hz, 2H), 7.54-7.52 (m, 2H), 7.49-7.47 (m, 3H), 7.38 (dd, J=4.8, 1.3 Hz, 1H), 7.33 (dd, J=8.2, 2.1 Hz, 1H), 7.26 (t, J=7.9 Hz, 2H), 7.01 (t, J=7.5 Hz, 1H), 6.78 (d, J=8.5 Hz, 1H), 6.08 (t, J=6.0 Hz, 1H), 5.77 (q, J=4.4 Hz, 1H), 5.00 (s, 2H), 4.01 (dd, J=9.1, 5.6 Hz, 1H), 3.52 (ddd, J=13.5, 8.8, 5.0 Hz, 1H), 3.42 (dt, J=12.8, 6.4 Hz, 1H), 2.51 (d, J=4.7 Hz, 3H). MS (ESI) calcd [M+H]+ 514.1, found 514.1.

Workup

  1. concentrationConcentration
  2. customyielded a yellow residue that
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-b91feb491e04406dabef5820d7fb347f
Source dataset
uspto-grants-2012_05
Patent number
US08168658B2

Reaction notes

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