Trifluoroacetic acid → HCID 57897287, compound

HRID 416863Notes

Reaction equation

HRID 416863 reaction equation
[Br:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][N:15]([CH:18]([C:20]3[CH:25]=[CH:24]C=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.[CH3:26][C:27]1C(CN2CCN(C(OC(C)(C)C)=O)CC2)=C(C)[O:29][N:28]=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[CH2:13][CH2:14][N:15]([CH2:18][C:20]3[C:27]([CH3:26])=[N:28][O:29][C:25]=3[CH3:24])[CH2:16][CH2:17]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 46743071HCID 46743071, compoundHCID 578971485-Bromo-3-nitro-4-(4-(1-(pyridin-2-yl)ethyl)piperazin-1-yl)pyridin-2-amine

Product 1

HCID 57897287HCID 57897287, 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-((3,5-dimethylisoxazol-4-yl)methyl)piperazine-1-carboxylate (1.1 eq, 0.35 mmol, 104 mg), TFA (1.25 mL) and CH2Cl2 (4 mL), then 5-bromo-4-chloro-3-nitropyridin-2-amine (81 mg, 0.32 mmol) in iPrOH (3 mL) and DIPEA (1 mL). Filtration and washing as previously described gave the product (105 mg, 72% for two steps) as a yellow solid; δH (500 MHz, DMSO-d6) 2.19 (s, 3H, CH3), 2.32 (s, 3H, CH3), 2.47 (s, br, 4H, piperazine N(CH2)2), 3.03 (s, br, 4H, piperazine N(CH2)2), 3.30 (s, hidden by DMSO peak, 2H, NCH2), 6.96 (s, br, 2H, NH2), 8.16 (s, 1H, bromopyridine H-6);

Workup

  1. customThis was prepared
  2. filtrationFiltration
  3. washwashing
  4. customas previously described gave the product (105 mg, 72% for two steps) as a yellow solid

Sources & evidence

ORD record
ord-300a6faaf2884a9dad84e27657da3ca4
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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