Dichloromethane → Benzamide

HRID 1643322Notes

Reaction equation

HRID 1643322 reaction equation
N[C:2]1[CH:34]=[CH:33][C:5]([C:6]([NH:8]C2C=C(C3SC=CC=3)C=CC=2N(CC(NC)=O)C(=O)OC(C)(C)C)=[O:7])=[CH:4][CH:3]=1.C(Cl)Cl>C(O)(C(F)(F)F)=O.CCOC(C)=O>[C:6]([NH2:8])(=[O:7])[C:5]1[CH:33]=[CH:34][CH:2]=[CH:3][CH:4]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 66757683HCID 66757683, compound

Product 1

HCID 2331Benzamide

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-butyl [2-[(4-aminobenzoyl)amino]-4-(2-thienyl)phenyl][2-(methylamino)-2-oxoethyl]carbamate was dissolved in 1:1 TFA:CH2Cl2 and stirred at room temperature for 1 hour. The crude reaction was diluted with EtOAc (20 mL) and washed with sat.'d aq. NaHCO3 (1×10 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo and gave the desired 4-amino-N-[2-{[2-methylamino)-2-oxoethyl]amino}-5-(2-thienyl)phenyl]benzamide: 1H NMR (600 MHz, DMSO-d6) δ 10.70 (s, 1H), 8.27 (d, J=4.5 Hz, 1H), 8.22 (d, J=2.1 Hz, 1H), 7.83 (d, J=8.6 Hz, 2H), 7.54 (d, J=3.4 Hz, 1H), 7.37 (dd, J=8.2, 2.1 Hz, 1H), 7.28 (d, J=8.2 Hz, 1H), 7.12 (dd, J=5.0, 3.7 Hz, 1H), 6.57 (d, J=8.6 Hz, 2H), 5.73 (s, 2H), 4.62 (d, J=16.8 Hz, 1H), 3.80 (d, J=16.9 Hz, 1H), 2.64 (d, J=4.5 Hz, 3H), 1.05 (s, 9H); MS: cal'd 381.1 (MH+), exp 381.1 (MH+).

Workup

  1. customThe crude reaction
  2. washwashed with sat.'d aq. NaHCO3 (1×10 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a8be0da3f91a47aa992f27a2a6fd6ab0
Source dataset
uspto-grants-2012_02
Patent number
US08119685B2

Reaction notes

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