Trifluoroacetic acid → HCID 178419433, compound

HRID 416837Notes

Reaction equation

HRID 416837 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:61]2[CH2:66][CH2:65][N:64]([CH2:67][C:68]3[CH:69]=[N:70][CH:71]=[CH:72][CH:73]=3)[CH2:63][CH2:62]2)=[C:35]2[N:41]=[C:40]([C:42]3[CH:47]=[CH:46][C:45]([N:48]4[CH2:53][CH2:52][N:51](C(OC(C)(C)C)=O)[CH2:50][CH2:49]4)=[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:61]2[CH2:62][CH2:63][N:64]([CH2:67][C:68]3[CH:69]=[N:70][CH:71]=[CH:72][CH:73]=3)[CH2:65][CH2:66]2)=[C:35]2[N:41]=[C:40]([C:42]3[CH:43]=[CH:44][C:45]([N:48]4[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]4)=[CH:46][CH:47]=3)[NH:39][C:36]2=[N:37][CH:38]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 178452226HCID 178452226, compoundHCID 178509626HCID 178509626, compound

Product 1

HCID 178419433HCID 178419433, compoundYield 75%

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-(4-(6-bromo-7-(4-(pyridin-3-ylmethyl)piperazin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)phenyl)piperazine-1-carboxylate (16 mg, 0.025 mmol), TFA (0.25 mL) and CH2Cl2 (1 mL). The same purification procedure gave the desired product (10 mg, 75%) as a pale yellow solid; δH (500 MHz, DMSO-d6) 2.50 (hidden by DMSO peak, 2H, piperazine NCH2), 2.62 (s, br, 4H, piperazine N(CH2)2), 3.00 (s, br, 2H, piperazine NCH2), 3.30 (hidden by DMSO peak, 4H, piperazine N(CH2)2), 3.61 (s, 2H, NCH2), 3.64 (s, br, 4H, piperazine N(CH2)2), 7.06 (d, J=8.9 Hz, 2H, phenyl H-3 & H-5), 7.39 (dd, J=7.7, 4.8 Hz, 1H, pyridine H-5), 7.78 (d, br, J=7.7 Hz, 1H, pyridine H-4), 8.03 (d, J=8.9 Hz, 2H, phenyl H-2 & H-6), 8.17 (s, 1H, imidazo[4,5-b]pyridine H-5), 8.49 (dd, J=4.7, 1.4 Hz, 1H, pyridine H-6), 8.56 (s, br, 1H, pyridine H-2), 13.23 (s, br, 1H, imidazo[4,5-b]pyridine NH);

Workup

  1. customThis was prepared
  2. customThe same purification procedure

Sources & evidence

ORD record
ord-28a1dbd183114c64b77079afbdc128fe
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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