Trifluoroacetic acid → HCID 24890104, compound

HRID 521642Notes

Reaction equation

HRID 521642 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.C(OC(=O)N([O:22][C:23]1[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][C:24]=1[C:30]1[N:31]([CH3:36])[N:32]=[CH:33][C:34]=1[Br:35])C(C)(C)C)(C)(C)C.C([N:41](CC)[CH:42]([CH3:44])[CH3:43])(C)C.[C:47](O)(C(F)(F)F)=O>ClCCl>[NH2:41][C:42]([CH3:44])([CH3:47])[CH2:43][O:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:25][C:24]=1[C:30]1[N:31]([CH3:36])[N:32]=[CH:33][C:34]=1[Br:35]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 678794-Fluorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 86730292HCID 86730292, compound

Product 1

HCID 24890104HCID 24890104, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Flurobenzoyl chloride (6.630-, 0.056 mmol) was added to a solution of tert-butyl(4-amino-2-(4-bromo-2-methyl-2H-pyrazol-3-yl)phenoxy)-2-methylpropan-2-ylcarbamate (0.25 mL of a 0.2M solution in dichloromethane, 0.050 mmol) and N,N-diisopropylethylamine (13.1 μL, 0.075 mmol) in dichloromethane (0.5 mL) and the reaction vessel was agitated on a mechanical shaker overnight. TFA (0.25 mL) was added, and the reaction vessel was shaken for another 30 min. The solvent was evaporated in vacuo, and the crude product was purified by RP-HPLC and lyophilized to give the title compound as a TFA-salt (26 mg, 92%). LCMS m/z (%)=463.2 (M+H 81Br 43%), 461.2 (M+H 79Br 43%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.09 (s, 3H), 1.11 (s, 3H), 3.60 (s, 3H), 3.76 (d, J=9.60 Hz, 1H), 3.92 (d, J=9.85 Hz, 1H), 7.21 (d, J=9.09 Hz, 1H), 7.27-7.36 (m, 2H), 7.60 (s, 1H), 7.62 (d, J=2.53 Hz, 1H), 7.86 (s, 3H), 7.87 (dd, J=9.09, 2.53 Hz, 1H), 7.93-8.00 (m, 2H), 10.30 (s, 1H).

Workup

  1. stirringthe reaction vessel was shaken for another 30 min
  2. customThe solvent was evaporated in vacuo
  3. customthe crude product was purified by RP-HPLC

Sources & evidence

ORD record
ord-bcb9793ecf3e42a38b7004997b93ca49
Source dataset
uspto-grants-2016_05
Patent number
US09328107B2

Reaction notes

Loading…