Trifluoroacetic acid → HCID 178510882, compound

HRID 416832Notes

Reaction equation

HRID 416832 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:52]2[CH2:57][CH2:56][N:55]([CH2:58][C:59]3[CH:60]=[N:61][CH:62]=[CH:63][CH:64]=3)[CH2:54][CH2:53]2)=[C:35]2[N:41]=[C:40]([CH2:42][CH2:43][NH:44]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:52]2[CH2:57][CH2:56][N:55]([CH2:58][C:59]3[CH:60]=[N:61][CH:62]=[CH:63][CH:64]=3)[CH2:54][CH2:53]2)=[C:35]2[N:41]=[C:40]([CH2:42][CH2:43][NH2:44])[NH:39][C:36]2=[N:37][CH:38]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 178453344HCID 178453344, compoundHCID 178509626HCID 178509626, compound

Product 1

HCID 178510882HCID 178510882, compoundYield 93%

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 2-(6-bromo-7-(4-(pyridin-3-ylmethyl)piperazin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)ethylcarbamate (20 mg, 0.058 mmol), TFA (0.2 mL) and CH2Cl2 (1 mL). The same purification procedure gave the desired product (15 mg, 93%) as a colourless solid; δH (500 MHz, DMSO-d6) 2.58 (s, br, 4H, piperazine N(CH2)2), 2.87 (t, J=6.7 Hz, 2H, CH2CH2NH2), 3.00 (t, J=6.8 Hz, 2H, CH2CH2NH2), 3.55 (t, J=4.5 Hz, 4H, piperazine N(CH2)2), 3.61 (s, 2H, NCH2Ar), 7.39 (dd, J=7.8, 4.8 Hz, 1H, pyridine H-5), 7.77 (d, br, J=7.8 Hz, 1H, pyridine H-4), 8.18 (s, 1H, imidazo[4,5-b]pyridine H-5), 4.49 (dd, J=4.7, 1.0 Hz, 1H, pyridine H-6), 8.55 (d, J=1.1 Hz, 1H, pyridine H-2);

Workup

  1. customThis was prepared
  2. customThe same purification procedure

Sources & evidence

ORD record
ord-1503a15647d948e99cbede0fbb8edd31
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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