Trifluoroacetic acid → 6-[[3-[[4-(2-Aminoethyl)phenyl]carbamoyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-3-carboxamide

HRID 1944914Notes

Reaction equation

HRID 1944914 reaction equation
C(O)(C(F)(F)F)=O.[C:8]([C:11]1[CH:12]=[N:13][C:14]2[C:19]([C:20]=1[NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=1)=[CH:18][C:17]([S:30]([C:33]1[CH:34]=[C:35]([CH:55]=[CH:56][CH:57]=1)[C:36]([NH:38][C:39]1[CH:54]=[CH:53][C:42]([CH2:43][CH2:44][NH:45]C(=O)OC(C)(C)C)=[CH:41][CH:40]=1)=[O:37])(=[O:32])=[O:31])=[CH:16][C:15]=2[CH3:58])(=[O:10])[NH2:9]>C(Cl)Cl>[NH2:45][CH2:44][CH2:43][C:42]1[CH:53]=[CH:54][C:39]([NH:38][C:36]([C:35]2[CH:34]=[C:33]([S:30]([C:17]3[CH:18]=[C:19]4[C:14](=[C:15]([CH3:58])[CH:16]=3)[N:13]=[CH:12][C:11]([C:8]([NH2:9])=[O:10])=[C:20]4[NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=3)(=[O:31])=[O:32])[CH:57]=[CH:56][CH:55]=2)=[O:37])=[CH:40][CH:41]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58505121tert-Butyl 4-[3-[[3-carbamoyl-4-[(3-methoxyphenyl)amino]-8-methylquinolin-6-yl]sulfonyl]benzamido]phenethylcarbamate

Product 1

HCID 585050736-[[3-[[4-(2-Aminoethyl)phenyl]carbamoyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.5 mL) was added dropwise to a suspension of Intermediate 82 (382 mg, 0.538 mmol) in CH2Cl2 (5 mL) at rt. After stirring for 5 h, the reaction was concentrated in vacuo to give a brown residue. A portion was treated with silica-carbonate resin and used in the following step without further purification. ES/MS calcd. for C33H32N5O5S+ 610.2. Found m/z=610.2 (M+H)+.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. customto give a brown residue
  3. additionA portion was treated with silica-carbonate resin
  4. customused in the following step without further purification

Sources & evidence

ORD record
ord-a31bfeea3a564c1abfe722026e7c93a4
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

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