Trifluoroacetic acid → HCID 57897304, compound

HRID 416859Notes

Reaction equation

HRID 416859 reaction equation
[Br:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][N:15]([CH:18](C3C=CC=CN=3)C)[CH2:14][CH2:13]2)=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([NH2:8])=[N:6][CH:7]=1.[F:26][C:27]([F:49])([F:48])[C:28]1[N:33]=[CH:32][C:31](CN2CCN(C(OC(C)(C)C)=O)CC2)=[CH:30][CH:29]=1.C(O)(C(F)(F)F)=O.BrC1C(Cl)=C([N+]([O-])=O)C(N)=NC=1>CC(O)C.CCN(C(C)C)C(C)C.C(Cl)Cl>[Br:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:31]3[CH:32]=[N:33][C:28]([C:27]([F:49])([F:48])[F:26])=[CH:29][CH:30]=3)[CH2:14][CH2:13]2)=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([NH2:8])=[N:6][CH:7]=1

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 454802365-Bromo-4-chloro-3-nitropyridin-2-amineHCID 578971485-Bromo-3-nitro-4-(4-(1-(pyridin-2-yl)ethyl)piperazin-1-yl)pyridin-2-amineHCID 57897218HCID 57897218, compound

Product 1

HCID 57897304HCID 57897304, compound

Reagents, catalysts & solvents 3

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolventHCID 81531DiisopropylethylamineSolvent

Procedure

This was prepared using the same procedure as for 5-bromo-3-nitro-4-(4-(1-(pyridin-2-yl)ethyl)piperazin-1-yl)pyridin-2-amine, but here using tert-butyl 4-((6-(trifluoromethyl)pyridin-3-yl)methyl)piperazine-1-carboxylate (1.1 eq, 0.27 mmol, 93 mg), TFA (1 mL) and CH2Cl2 (3 mL), then 5-bromo-4-chloro-3-nitropyridin-2-amine (62 mg, 0.24 mmol) in iPrOH (3 mL) and DIPEA (1 mL). Filtration and washing as previously described gave the product (78 mg, 63% for two steps) as a yellow solid; δH (500 MHz, DMSO-d6) 2.55 (s, br, 4H, piperazine N(CH2)2), 3.07 (s, br, 4H, piperazine N(CH2)2), 3.69 (s, 2H, NCH2), 6.97 (s, br, 2H, NH2), 7.87 (d, J=8.0 Hz, 1H, pyridine H-5), 8.03 (dd, J=8.0, 0.6 Hz, 1H, pyridine H-4), 8.16 (s, 1H, bromopyridine H-6), 8.71 (d, J=0.6 Hz, 1H, pyridine H-2);

Workup

  1. customThis was prepared
  2. filtrationFiltration
  3. washwashing
  4. customas previously described gave the product (78 mg, 63% for two steps) as a yellow solid

Sources & evidence

ORD record
ord-502e278a861b41a099192da8532850b9
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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