Trifluoroacetic acid → HCID 57897141, compound

HRID 416853Notes

Reaction equation

HRID 416853 reaction equation
[Br:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][N:15](C(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.[O:26]1[C:30]2[CH:31]=[CH:32][CH:33]=[C:34]([CH2:35]N3CCN(C(OC(C)(C)C)=O)CC3)[C:29]=2[O:28][CH2:27]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>[O:26]1[C:30]2[CH:31]=[CH:32][CH:33]=[C:34]([CH2:35][N:15]3[CH2:16][CH2:17][N:12]([C:3]4[C:2]([Br:1])=[CH:7][N:6]=[C:5]([NH2:8])[C:4]=4[N+:9]([O-:11])=[O:10])[CH2:13][CH2:14]3)[C:29]=2[O:28][CH2:27]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 57897236HCID 57897236, compound

Product 1

HCID 57897141HCID 57897141, 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-(benzo[d][1,3]dioxol-4-ylmethyl)piperazine-1-carboxylate (1.1 eq, 0.37 mmol, 120 mg), TFA (1.5 mL) and CH2Cl2 (3 mL), then 5-bromo-4-chloro-3-nitropyridin-2-amine (86 mg, 0.34 mmol) in iPrOH (3.5 mL) and DIPEA (1 mL). Filtration and washing as previously described gave the product (131 mg, 80% for two steps) as a yellow solid; δH (500 MHz, DMSO-d6) 2.54 (s, br, 4H, piperazine N(CH2)2), 3.06 (s, br, 4H, piperazine N(CH2)2), 3.51 (s, 2H, NCH2), 6.00 (s, 2H, OCH2), 6.83-6.85 (m, 3H, phenyl H-4, H-5, H-6), 6.98 (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 (131 mg, 80% for two steps) as a yellow solid

Sources & evidence

ORD record
ord-83dd3eb225604be4925da042646fdd3a
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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