Trifluoroacetic acid → HCID 178509709, compound

HRID 416827Notes

Reaction equation

HRID 416827 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:57]2[CH2:62][CH2:61][N:60]([CH2:63][C:64]3[CH:65]=[N:66][CH:67]=[CH:68][CH:69]=3)[CH2:59][CH2:58]2)=[C:35]2[N:41]=[C:40]([C:42]3[CH:43]=[C:44]([CH:54]=[CH:55][CH:56]=3)[CH2:45][NH:46]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:57]2[CH2:58][CH2:59][N:60]([CH2:63][C:64]3[CH:65]=[N:66][CH:67]=[CH:68][CH:69]=3)[CH2:61][CH2:62]2)=[C:35]2[N:41]=[C:40]([C:42]3[CH:43]=[C:44]([CH2:45][NH2:46])[CH:54]=[CH:55][CH:56]=3)[NH:39][C:36]2=[N:37][CH:38]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 178453047HCID 178453047, compoundHCID 178509626HCID 178509626, compound

Product 1

HCID 178509709HCID 178509709, compoundYield 85.4%

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 3-(6-bromo-7-(4-(pyridin-3-ylmethyl)piperazin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)benzylcarbamate (70 mg, 0.12 mmol), TFA (0.6 mL) and CH2Cl2 (2 mL). The same purification procedure gave the desired product (49 mg, 84%) as a colourless solid; δH (500 MHz, DMSO-d6) 2.63 (s, br, 4H, piperazine N(CH2)2), 3.63 (s, 2H, NCH2Ar), 3.68 (t, J=4.3 Hz, 4H, piperazine N(CH2)2), 3.84 (s, 2H, CH2NH2), 7.40 (dd, J=7.7, 4.8 Hz, 1H, pyridine H-5), 7.48-7.50 (m, 2H, phenyl H-4 & H-6), 7.80 (dt, J=7.7, 1.7 Hz, 1H, pyridine H-4), 8.02-8.05 (m, 1H, phenyl H-5), 8.18 (s, br, 1H, phenyl H-2), 8.25 (s, 1H, imidazo[4,5-b]pyridine H-5), 8.50 (dd, J=4.8, 1.5 Hz, 1H, pyridine H-6), 8.58 (d, J=1.6 Hz, 1H, pyridine H-2);

Workup

  1. customThis was prepared
  2. customThe same purification procedure

Sources & evidence

ORD record
ord-411d615e4edf45e98257a82827f87c0a
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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