Trifluoroacetic acid → HCID 178432922, compound

HRID 416917Notes

Reaction equation

HRID 416917 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[NH:43][C:24]4=[N:25][CH:26]=[C:27]([Br:42])[C:28]([N:29]5[CH2:34][CH2:33][N:32]([CH2:35][C:36]6[N:37]=[C:38]([CH3:41])[S:39][CH:40]=6)[CH2:31][CH2:30]5)=[C:23]4[N:22]=3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:42][C:27]1[C:28]([N:29]2[CH2:30][CH2:31][N:32]([CH2:35][C:36]3[N:37]=[C:38]([CH3:41])[S:39][CH:40]=3)[CH2:33][CH2:34]2)=[C:23]2[N:22]=[C:21]([C:18]3[CH:19]=[CH:20][C:15]([CH2:14][N:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)=[CH:16][CH:17]=3)[NH:43][C:24]2=[N:25][CH:26]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178432923HCID 178432923, compound

Product 1

HCID 178432922HCID 178432922, compoundYield 91%

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)benzyl)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), washed with methanol and then eluted with ammonia (0.2M) in methanol. The filtrate was collected and the solvent removed in vacuo to give the title compound as a off-white solid (0.017 g, 91%); 1H-NMR (500 Mz, DMSO-d6): δ 2.26-2.36 (m, 4H), 2.61-2.75 (m, 11H), 3.50 (s, 2H, NCH2), 3.61-3.70 (m, 6H), 7.32 (s, 1H, thiazole 5-H), 7.45 (d, J=8.5 Hz, 2H, ArH, C6H4), 8.13 (d, J=8.05 Hz, 2H, ArH, C6H4), 8.23 (s, 1H, imidazo[4,5-b]pyridine 5-H); LC (Method B)-MS (ESI, m/z) 2.19 min—567/569 [(M+H)+, Br isotopic pattern]; ESI-HRMS: Found: 567.1634, calculated for C26H32N8SBr (M+H)+: 567.1654.

Workup

  1. temperaturethe mixture cooled in an ice bath
  2. washwashed with methanol
  3. washeluted with ammonia (0.2M) in methanol
  4. customThe filtrate was collected
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-50808c1deb5a40a7a4ee7d64204c51f0
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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