Trifluoroacetic acid → HCID 178509624, compound

HRID 416869Notes

Reaction equation

HRID 416869 reaction equation
BrC1C(N2CCN(CC3C=NC=CC=3)CC2)=C2N=C(C3C=CC(CN)=CC=3)NC2=NC=1.[CH2:32]([CH:39]1[CH2:44][CH2:43][N:42]([C:45]2[C:50]([Br:51])=[CH:49][N:48]=[C:47]3[NH:52][C:53]([C:55]4[CH:69]=[CH:68][C:58]([CH2:59][NH:60]C(=O)OC(C)(C)C)=[CH:57][CH:56]=4)=[N:54][C:46]=23)[CH2:41][CH2:40]1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:32]([CH:39]1[CH2:40][CH2:41][N:42]([C:45]2[C:50]([Br:51])=[CH:49][N:48]=[C:47]3[NH:52][C:53]([C:55]4[CH:69]=[CH:68][C:58]([CH2:59][NH2:60])=[CH:57][CH:56]=4)=[N:54][C:46]=23)[CH2:43][CH2:44]1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 178453032tert-butyl 4-(7-(4-benzylpiperidin-1-yl)-6-bromo-3H-imidazo[4,5-b]pyridin-2-yl)benzylcarbamateHCID 178509626HCID 178509626, compound

Product 1

HCID 178509624HCID 178509624, compoundYield 97%

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-(7-(4-benzylpiperidin-1-yl)-6-bromo-3H-imidazo[4,5-b]pyridin-2-yl)benzylcarbamate (15 mg, 0.026 mmol), TFA (0.2 mL) and CH2Cl2 (1 mL). The same purification procedure gave the desired product (12 mg, 97%) as a colourless solid; δH (500 MHz, DMSO-d6) 1.40-1.48 (m, 2H, 2× piperidine CHAHB), 1.73 (d, br, J=11.7 Hz, 2H, 2× piperidine CHAHB), 1.79-1.85 (m, 1H, piperidine CH), 2.61 (app d, J=7.1 Hz, 2H, PhCH2), 3.31-3.36 (m, 2H, 2× piperidine NCHAHA), 3.79 (s, 2H, CH2NH2), 3.85 (app d, J=12.0 Hz, 2H, 2× piperidine NCHAHA), 7.20 (t, J=7.2 Hz, 1H, phenyl H-4), 7.23 (d, J=7.0 Hz, 2H, phenyl H-2 & H-6), 7.31 (t, J=7.5 Hz, 2H, phenyl H-3 & H-5), 7.48 (d, J=8.2 Hz, 2H, phenyl H-3′ & H-5′), 8.10 (d, J=8.2 Hz, 2H, phenyl H-2′ & H-6′), 8.21 (s, 1H, (s, 1H, imidazo[4,5-b]pyridine H-5).

Workup

  1. customThis was prepared
  2. customThe same purification procedure

Sources & evidence

ORD record
ord-305bdb14fe234e29a0b3dbc633e58cf4
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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