Trifluoroacetic acid → HCID 44442354, compound

HRID 1694842Notes

Reaction equation

HRID 1694842 reaction equation
[NH:1]([C:8](=[O:43])[C:9]([C:20]1[CH:42]=[CH:41][C:23]([C:24]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[NH:33]C(=O)OC(C)(C)C)=[O:25])=[CH:22][CH:21]=1)([C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:12])[F:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[NH:26][C:24]([C:23]1[CH:22]=[CH:21][C:20]([C:9]([F:10])([C:8]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:43])[C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:12])=[CH:42][CH:41]=1)=[O:25]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59376445HCID 59376445, compound

Product 1

HCID 44442354HCID 44442354, compoundYield 22.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl [2-({4-[2-anilino-1-(anilinocarbonyl)-1-fluoro-2-oxoethyl]benzoyl}amino)phenyl]carbamate (11 mg, 0.019 mmol) in CH2Cl2 (3 mL) at room temperature was added trifluoroacetic acid (1 mL). The reaction mixture was stirred at room temperature 45 min and concentrated. Purification by reverse phase HPLC (10% to 80% MeCN in water) gave 2-(4-{[(2-aminophenyl)amino]carbonyl}phenyl)-2-fluoro-N,N′-diphenylmalonamide (2.1 mg, TFA salt, 19%) as a white solid: 1H NMR (600 MHz, CD3OD) δ 8.13 (d, J=8.2 Hz, 2H), 7.95 (d, J=8.5 Hz, 2H), 7.64-7.62 (m, 4H), 7.41-7.35 (m, 8H), 7.18 (t, J=7.6 Hz, 2H); ESIMS calcd 483.2 (M++H), found 483.1 (M++H). General Procedure for the Synthesis of Non-Symmetrical Malonamide Benzamides

Workup

  1. concentrationconcentrated
  2. customPurification by reverse phase HPLC (10% to 80% MeCN in water)

Sources & evidence

ORD record
ord-cd7a30a9de404334a387cf29e779da3e
Source dataset
uspto-grants-2012_04
Patent number
US08158825B2

Reaction notes

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