Trifluoroacetic acid → HCID 178432926, compound

HRID 416916Notes

Reaction equation

HRID 416916 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[NH:42][C:23]4=[N:24][CH:25]=[C:26]([Br:41])[C:27]([N:28]5[CH2:33][CH2:32][N:31]([CH2:34][C:35]6[N:36]=[C:37]([CH3:40])[S:38][CH:39]=6)[CH2:30][CH2:29]5)=[C:22]4[N:21]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:41][C:26]1[C:27]([N:28]2[CH2:29][CH2:30][N:31]([CH2:34][C:35]3[N:36]=[C:37]([CH3:40])[S:38][CH:39]=3)[CH2:32][CH2:33]2)=[C:22]2[N:21]=[C:20]([C:17]3[CH:18]=[CH:19][C:14]([N:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)=[CH:15][CH:16]=3)[NH:42][C:23]2=[N:24][CH:25]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178432927tert-Butyl 4-(4-(6-bromo-7-(4-((2-methylthiazol-4-yl)methyl)piperazin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)phenyl)piperazine-1-carboxylate

Product 1

HCID 178432926HCID 178432926, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl-4-(4-(6-bromo-7-(4-((2-methylthiazol-4-yl)methyl)piperazin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)phenyl)piperazine-1-carboxylate (0.022 g, 0.033 mmol) was suspended in DCM (2.0 mL) and the mixture cooled in an ice bath. TFA (0.5 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 (5 g), the filtrate collected and the solvent removed in vacuo to give the title compound as a solid (0.016 g, 86%); 1H-NMR (500 Mz, DMSO-d6): δ 2.61-2.70 (m, 7H), 2.81-2.89 (m, 4H), 3.15-3.22 (m, 4H), 3.60-3.68 (m, 6H), 7.03 (d, J=9.0 Hz, 2H, ArH, C6H4), 7.32 (s, 1H, thiazole 5-H), 8.02 (d, J=9.0 Hz, 2H, ArH, C6H4), 8.17 (s, 1H, imidazo[4,5-b]pyridine 5-H); LC (Method B)-MS (ESI, m/z) 2.23 min—553/555 [(M+H)+, Br isotopic pattern]. ESI-HRMS: Found: 553.1522, calculated for C25H30BrN8S (M+H)+: 553.1498.

Workup

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

Sources & evidence

ORD record
ord-0a174505ef054c12854574756dd0ab5d
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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