Trifluoroacetic acid → HCID 178509625, compound

HRID 416872Notes

Reaction equation

HRID 416872 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][CH:60]([O:63][C:64]3[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=3)[CH2:59][CH2:58]2)=[C:35]2[N:41]=[C:40]([C:42]3[CH:56]=[CH:55][C:45]([CH2:46][NH:47]C(=O)OC(C)(C)C)=[CH:44][CH:43]=3)[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[CH2:62][CH2:61][CH:60]([O:63][C:64]3[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=3)[CH2:59][CH2:58]2)=[C:35]2[N:41]=[C:40]([C:42]3[CH:43]=[CH:44][C:45]([CH2:46][NH2:47])=[CH:55][CH:56]=3)[NH:39][C:36]2=[N:37][CH:38]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 178453033HCID 178453033, compoundHCID 178509626HCID 178509626, compound

Product 1

HCID 178509625HCID 178509625, compoundYield 93.7%

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 4-(6-bromo-7-(4-phenoxypiperidin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)benzylcarbamate (17 mg, 0.029 mmol), TFA (0.25 mL) and CH2Cl2 (1 mL). The same purification procedure gave the desired product (13 mg, 93%) as a colourless solid; δH (500 MHz, DMSO-d6) 1.84-1.90 (m, 2H, 2× piperidine CHAHB), 2.17-2.19 (m, 2H, 2× piperidine CHAHB), 3.61 (ddd, J=12.4, 9.7, 1.8 Hz, 2× piperidine NCHAHA), 3.80 (s, 3H, OCH3), 3.86-3.91 (m, 2H, 2× piperidine NCHAHA), 4.70 (septet, J=4.0 Hz, 1H, piperidine CH), 6.94 (t, J=7.3 Hz, 1H, phenyl H-4), 7.04 (d, J=7.8 Hz, 2H, phenyl H-2 & H-6), 7.30 (dd, J=8.6, 7.4 Hz, 2H, phenyl H-3 & H-5), 7.50 (d, J=8.6 Hz, 2H, phenyl H-3′ & H-5′), 8.11 (d, J=8.4 Hz, 2H, phenyl H-2′ & H-6′), 8.23 (s, 1H, imidazo[4,5-b]pyridine H-5);

Workup

  1. customThis was prepared
  2. customThe same purification procedure

Sources & evidence

ORD record
ord-4441447771c04f43945170df7bac0f94
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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