Trifluoroacetic acid → HCID 59451456, compound

HRID 1874822Notes

Reaction equation

HRID 1874822 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH:16][C:17]([C:19]2[NH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][C:22]=3[NH:28]C(=O)OC(C)(C)C)=[O:18])=[C:11]([F:36])[C:10]=1[O:37][C:38]1[CH:43]=[C:42]([C:44]#[N:45])[CH:41]=[C:40]([Cl:46])[CH:39]=1>ClCCl>[NH2:28][C:22]1[CH:23]=[CH:24][CH:25]=[C:26]2[C:21]=1[NH:20][C:19]([C:17]([NH:16][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([Cl:8])=[C:10]([O:37][C:38]3[CH:43]=[C:42]([C:44]#[N:45])[CH:41]=[C:40]([Cl:46])[CH:39]=3)[C:11]=1[F:36])=[O:18])=[CH:27]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59451347HCID 59451347, compound

Product 1

HCID 59451456HCID 59451456, compoundYield 51.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.028 mL, 0.369 mmol) was added to a solution of 1,1-dimethylethyl (2-{[({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)amino]carbonyl}-1H-indol-7-yl)carbamate (0.021 g, 0.037 mmol) in dichloromethane. The mixture was stirred at RT overnight. The solvent was evaporated and the residue was purified by Reverse-Phase HPLC (water/acetonitrile with 0.1% TFA) to give the title compound (0.009 g, 45%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 11.46 (s, 1H), 9.07 (s, 1H), 7.81 (s, 1H), 7.43-7.58 (m, 3H), 7.32-7.43 (m, 1H), 7.09-7.22 (m, 2H), 6.82-6.97 (m, 1H), 6.62-6.75 (m, 1H), 4.58 (s, 2H), 4.20 (br s, 2H). MS: m/z 469 (M+1).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by Reverse-Phase HPLC (water/acetonitrile with 0.1% TFA)

Sources & evidence

ORD record
ord-1b8acc5a6a754f1f817d8e893123e387
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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