Trifluoroacetic acid → HCID 178481241, compound

HRID 416944Notes

Reaction equation

HRID 416944 reaction equation
[Br:1][C:2]1[C:3]([N:31]2[CH2:36][CH2:35][N:34]([CH2:37][C:38]3[N:42]([CH3:43])[CH:41]=[N:40][CH:39]=3)[CH2:33][CH2:32]2)=[C:4]2[N:10]=[C:9]([C:11]3[CH:30]=[CH:29][C:14]([CH2:15][N:16]4[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]4)=[CH:13][CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[C:3]([N:31]2[CH2:32][CH2:33][N:34]([CH2:37][C:38]3[N:42]([CH3:43])[CH:41]=[N:40][CH:39]=3)[CH2:35][CH2:36]2)=[C:4]2[N:10]=[C:9]([C:11]3[CH:30]=[CH:29][C:14]([CH2:15][N:16]4[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]4)=[CH:13][CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178481242HCID 178481242, compound

Product 1

HCID 178481241HCID 178481241, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(4-(6-bromo-7-(4-((1-methyl-1H-imidazol-5-yl)methyl)piperazin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)benzyl)piperazine-1-carboxylate (0.028 g, 0.043 mmol) was suspended in DCM (2.3 mL) and the mixture cooled in an ice bath. TFA (0.56 mL) was added and the resulting solution was allowed to warm up to room temperature and stirred for 2 h. The mixture was passed through an SCX column (2 g), the filtrate collected and the solvent removed in vacuo to give the title compound as a off-white solid (0.021 g, 89%); 1H-NMR (500 Mz, DMSO-d6): 2.27-2.36 (m, 4H), 2.55-2.62 (m, 4H), 2.72 (t, J=4.8 Hz, 4H), 3.50 (s, 2H, NCH2), 3.54 (s, 2H, NCH2), 3.61-3.66 (m, 4H), 3.68 (s, 3H, imidazole Me), 6.80 (s, 1H, imidazole 4-H), 7.45 (d, J=8.0 Hz, 2H, ArH, C6H4), 7.57 (s, 1H, imidazole 2-H), 8.14 (d, J=8.5 Hz, 2H, ArH, C6H4), 8.23 (s, 1H, imidazo[4,5-b]pyridine 5-H); LC (Method B)-MS (ESI, m/z) 1.66 min—550/552 [(M+H)+], Br isotopic pattern]; ESI-HRMS: Found: 550.2044, calculated for C26H33BrN9 (M+H)+: 550.2042.

Workup

  1. temperaturethe mixture cooled in an ice bath
  2. customthe filtrate collected
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-e8c8cd6aca9442fd9df0c37e74293182
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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