Trifluoroacetic acid → HCID 57942139, compound

HRID 1898186Notes

Reaction equation

HRID 1898186 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9](=[O:41])[NH:10][C:11]1[CH:16]=[C:15]([C:17]([C:19]2[C:24]([NH:25][S:26]([C:29]3[CH:34]=[CH:33][C:32]([CH3:35])=[C:31]([C:36]([F:39])([F:38])[F:37])[CH:30]=3)(=[O:28])=[O:27])=[CH:23][C:22]([Cl:40])=[CH:21][N:20]=2)=[O:18])[CH:14]=[CH:13][N:12]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH2:8][C:9]([NH:10][C:11]1[CH:16]=[C:15]([C:17]([C:19]2[C:24]([NH:25][S:26]([C:29]3[CH:34]=[CH:33][C:32]([CH3:35])=[C:31]([C:36]([F:37])([F:39])[F:38])[CH:30]=3)(=[O:28])=[O:27])=[CH:23][C:22]([Cl:40])=[CH:21][N:20]=2)=[O:18])[CH:14]=[CH:13][N:12]=1)=[O:41]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66648935HCID 66648935, compound

Product 1

HCID 57942139HCID 57942139, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ({-4-[5-chloro-3-(4-methyl-3-trifluoromethyl-benzenesulfonylamino)-pyridine-2-carbonyl]-pyridin-2-ylcarbamoyl}-methyl)-carbamic acid tert-butyl ester (45 mg) in CH2Cl2 was added TFA (200 L). The resulting mixture was stirred at room temperature for 3 h, concentrated under reduced pressure and the residue was re-dissolved in MeCN and purified by HPLC to provide 2-amino-N-{4-[5-chloro-3-(4-methyl-3-trifluoromethyl-benzenesulfonylamino)-pyridine-2-carbonyl]-pyridin-2-yl}-acetamide. 1H NMR (400 MHz, DMSO-d6) δ 11.16 (s, 1H), 8.48-8.46 (m, 1H), 8.19 (s, 1H), 8.08 (br m, 3H), 7.89 (s, 1H), 7.78-7.76 (m, 2H), 7.55 (d, J=7.6 Hz, 1H), 7.28-7.26 (m, 1H), 3.85 (s, 2H), 2.43 (s, 3H); MS m/z 528.0 (M+H)+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionthe residue was re-dissolved in MeCN
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-e1a189b3d4a5496da3d524f5664766c3
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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