Trifluoroacetic acid → HCID 178432930, compound

HRID 416937Notes

Reaction equation

HRID 416937 reaction equation
[Cl:1][C:2]1[C:3]([N:31]2[CH2:36][CH2:35][N:34]([CH2:37][C:38]3[N:39]=[C:40]([CH3:43])[S:41][CH:42]=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>[Cl:1][C:2]1[C:3]([N:31]2[CH2:32][CH2:33][N:34]([CH2:37][C:38]3[N:39]=[C:40]([CH3:43])[S:41][CH:42]=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 178432931HCID 178432931, compound

Product 1

HCID 178432930HCID 178432930, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(4-(6-chloro-7-(4-((2-methylthiazol-4-yl)methyl)piperazin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)benzyl)piperazine-1-carboxylate (0.009 g, 0.036 mmol) was suspended in DCM (1.0 mL) and the mixture cooled in an ice bath. TFA (0.3 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), washed with methanol and further eluted with ammonia (35% solution in water, 0.2M). The filtrate was collected and the solvent removed in vacuo to give the title compound as a solid (0.004 g, 21%); 1H-NMR (500 Mz, DMSO-d6): δ 2.41-2.49 (m, 4H), 2.62-2.70 (m, 7H), 2.87-2.94 (m, 4H), 3.56 (s, 2H, NCH2), 3.64 (s, 2H, NCH2), 3.67-3.74 (m, 4H), 7.32 (s, 1H, thiazole 5-H), 7.47 (d, J=8.0 Hz, 2H, ArH, C6H4), 8.11 (s, 1H, imidazo[4,5-b]pyridine 5-H), 8.13 (d, J=8.0 Hz, 2H, ArH, C6H4); LC (Method B)-MS (ESI, m/z) 2.09 min—523/525 [(M+H)+, Cl isotopic pattern]. ESI-HRMS: Found: 523.2155, calculated for C26H32ClN8S (M+H)+: 523.2159;

Workup

  1. temperaturethe mixture cooled in an ice bath
  2. washwashed with methanol
  3. washfurther eluted with ammonia (35% solution in water, 0.2M)
  4. customThe filtrate was collected
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-feb1673609be4423b26149627a95bbc4
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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