Trifluoroacetic acid → HCID 44442357, compound

HRID 1694840Notes

Reaction equation

HRID 1694840 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])[CH3:10])[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:41]=[CH:42][C:20]([C:9]([CH3:10])([C:8]([NH:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:43])[C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:12])=[CH:21][CH:22]=1)=[O:25]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59376452HCID 59376452, compound

Product 1

HCID 44442357HCID 44442357, compoundYield 104.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl [2-({4-[2-anilino-1-(anilinocarbonyl)-1-methyl-2-oxoethyl]benzoyl}amino)phenyl]-carbamate (14 mg, 0.024 mmol) in CH2Cl2 (3 mL) at room temperature was added trifluoroacetic acid (1 mL). The reaction mixture was stirred at room temperature 30 min and concentrated. Purification by reverse phase HPLC (10% to 95% MeCN in water) gave 2-(4-{[(2-aminophenyl)amino]carbonyl}-phenyl)-2-methyl-N,N′-diphenylmalonamide (12 mg, TFA salt, 84%) as a white solid: 1H NMR (600 MHz, CDCl3) δ 9.77 (s br, 1H), 9.18 (s br, 2H), 7.87 (d, J=6.2 Hz, 21-1), 7.45-7.42 (m, 6H), 7.34-7.28 (m, 5H), 7.17-7.04 (m, 5H), 6.18 (s br, 21-1), 2.05 (s, 3H); ESIMS calcd 479.2 (M++H), found 479.2 (M++H).

Workup

  1. concentrationconcentrated
  2. customPurification by reverse phase HPLC (10% to 95% MeCN in water)

Sources & evidence

ORD record
ord-2e5b9bda011d4840be4b6788738c0308
Source dataset
uspto-grants-2012_04
Patent number
US08158825B2

Reaction notes

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