Trifluoroacetic acid → HCID 178510552, compound

HRID 416833Notes

Reaction equation

HRID 416833 reaction equation
BrC1C(N2CCN(CC3C=NC=CC=3)CC2)=C2N=C(C3C=CC(CN)=CC=3)NC2=NC=1.[Br:32][C:33]1[C:34]([N:51]2[CH2:56][CH2:55][N:54]([CH2:57][C:58]3[CH:59]=[N:60][CH:61]=[CH:62][CH:63]=3)[CH2:53][CH2:52]2)=[C:35]2[N:41]=[C:40]([CH2:42][NH:43]C(=O)OC(C)(C)C)[NH:39][C:36]2=[N:37][CH:38]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:32][C:33]1[C:34]([N:51]2[CH2:52][CH2:53][N:54]([CH2:57][C:58]3[CH:59]=[N:60][CH:61]=[CH:62][CH:63]=3)[CH2:55][CH2:56]2)=[C:35]2[N:41]=[C:40]([CH2:42][NH2:43])[NH:39][C:36]2=[N:37][CH:38]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 178453119HCID 178453119, compoundHCID 178509626HCID 178509626, compound

Product 1

HCID 178510552HCID 178510552, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This was prepared using the same procedure as for (4-(6-bromo-7-(4-(pyridin-3-ylmethyl)piperazin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)phenyl)methanamine, but here using tert-butyl (6-bromo-7-(4-(pyridin-3-ylmethyl)piperazin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)methylcarbamate (10 mg, 0.020 mmol), TFA (0.2 mL) and CH2Cl2 (1 mL). The same purification procedure gave the desired product (7 mg, 88%) as a colourless solid; δH (500 MHz, DMSO-d6) 2.60 (s, br, 4H, piperazine N(CH2)2), 3.57 (s, br, 4H, piperazine N(CH2)2), 3.62 (s, 2H, NCH2Ar), 4.04 (s, br, 2H, CH2NH2), 7.38 (dd, J=7.7, 4.7 Hz, 1H, pyridine H-5), 7.77 (dt, J=7.8, 1.7 Hz, 1H, pyridine H-4), 8.24 (s, 1H, imidazo[4,5-b]pyridine H-5), 8.50 (dd, J=4.7, 1.5 Hz, 1H, pyridine H-6), 8.56 (d, J=1.6 Hz, 1H, pyridine H-2);

Workup

  1. customThis was prepared
  2. customThe same purification procedure

Sources & evidence

ORD record
ord-bcf898860c0e4c1bbcf2295e467aacf4
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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