Trifluoroacetic acid → 6-Chloro-2-(4-(piperazin-1-ylmethyl)phenyl)-7-(4-(pyrimidin-5-ylmethyl)piperazin-1-yl)-3H-imidazo[4,5-b]pyridine

HRID 416879Notes

Reaction equation

HRID 416879 reaction equation
BrC1C(N2CCN(CC3C=NC=CC=3)CC2)=C2N=C(C3C=CC(CN)=CC=3)NC2=NC=1.[Cl:32][C:33]1[C:34]([N:62]2[CH2:67][CH2:66][N:65]([CH2:68][C:69]3[CH:70]=[N:71][CH:72]=[N:73][CH:74]=3)[CH2:64][CH2:63]2)=[C:35]2[N:41]=[C:40]([C:42]3[CH:61]=[CH:60][C:45]([CH2:46][N:47]4[CH2:52][CH2:51][N:50](C(OC(C)(C)C)=O)[CH2:49][CH2:48]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>[Cl:32][C:33]1[C:34]([N:62]2[CH2:63][CH2:64][N:65]([CH2:68][C:69]3[CH:70]=[N:71][CH:72]=[N:73][CH:74]=3)[CH2:66][CH2:67]2)=[C:35]2[N:41]=[C:40]([C:42]3[CH:61]=[CH:60][C:45]([CH2:46][N:47]4[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]4)=[CH:44][CH:43]=3)[NH:39][C:36]2=[N:37][CH:38]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 178452296HCID 178452296, compoundHCID 178509626HCID 178509626, compound

Product 1

HCID 1784782666-Chloro-2-(4-(piperazin-1-ylmethyl)phenyl)-7-(4-(pyrimidin-5-ylmethyl)piperazin-1-yl)-3H-imidazo[4,5-b]pyridineYield 56%

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-chloro-7-(4-(pyrimidin-5-ylmethyl)piperazin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)benzyl)piperazine-1-carboxylate (15 mg, 0.025 mmol), TFA (0.2 mL) and CH2Cl2 (1 mL). The same purification procedure gave the desired product (7 mg, 56%) as a pale yellow solid; δH (500 MHz, DMSO-d6) 2.32 (s, br, 4H, piperazine N(CH2)2), 2.64 (s, br, 4H, piperazine N(CH2)2), 2.72 (t, J=4.6 Hz, 4H, piperazine N(CH2)2), 3.50 (s, 2H, NCH2), 3.64 (s, 2H, NCH2), 3.70 (t, J=4.5 Hz, 4H, piperazine N(CH2)2), 7.45 (d, J=8.2 Hz, 2H, phenyl H-3 & H-5), 8.11 (s, 1H, imidazo[4,5-b]pyridine H-5), 8.12 (d, J=8.3 Hz, 2H, phenyl H-2 & H-6), 8.80 (s, 2H, pyrimidine H-4 & H-6), 9.12 (s, 1H, pyrimidine H-2);

Workup

  1. customThis was prepared
  2. customThe same purification procedure

Sources & evidence

ORD record
ord-cf9a73cb9f934430ba2bfb8ac1059ac1
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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