Trifluoroacetic acid → 5-Bromo-3-nitro-4-(4-(1-(pyridin-4-yl)ethyl)piperazin-1-yl)pyridin-2-amine

HRID 416779

反応式

HRID 416779 の反応式
[Br:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][N:15]([CH:18](C3C=CC=CN=3)[CH3:19])[CH2:14][CH2:13]2)=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([NH2:8])=[N:6][CH:7]=1.[N:26]1[CH:31]=[CH:30][C:29](C(N2CCN(C(OC(C)(C)C)=O)CC2)C)=[CH:28][CH: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>[Br:1][C:2]1[C:3]([N:12]2[CH2:13][CH2:14][N:15]([CH:18]([C:29]3[CH:30]=[CH:31][N:26]=[CH:27][CH:28]=3)[CH3:19])[CH2:16][CH2:17]2)=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([NH2:8])=[N:6][CH:7]=1

参加物

8

反応物 4

HCID 6422Trifluoroacetic acidHCID 454802365-Bromo-4-chloro-3-nitropyridin-2-amineHCID 46868084tert-Butyl 4-(1-(pyridin-4-yl)ethyl)piperazine-1-carboxylateHCID 578971485-Bromo-3-nitro-4-(4-(1-(pyridin-2-yl)ethyl)piperazin-1-yl)pyridin-2-amine

生成物 1

HCID 468683495-Bromo-3-nitro-4-(4-(1-(pyridin-4-yl)ethyl)piperazin-1-yl)pyridin-2-amine

試薬・触媒・溶媒 3

HCID 3776Isopropanol溶媒HCID 6344Dichloromethane溶媒HCID 81531Diisopropylethylamine溶媒

実験手順

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-(1-(pyridin-4-yl)ethyl)piperazine-1-carboxylate (1.1 eq, 1.12 mmol, 327 mg), TFA (5 mL) and CH2Cl2 (5 mL), then 5-bromo-4-chloro-3-nitropyridin-2-amine (257 mg, 1.02 mmol) in iPrOH (5 mL) and DIPEA (2 mL). Filtration and washing as previously described gave the product (265 mg, 58% for two steps) as a yellow solid; 1H-NMR (500 MHz, DMSO-d6) 1.29 (d, J=6.8 Hz, CH3), 2.46-2.56 (2 m, 4H, piperazine N(CH2)2), 3.05 (s, br, 4H, piperazine N(CH2)2), 3.53 (q, J=6.7 Hz, 1H, CH), 6.96 (s, br, 2H, NH2), 7.34 (dd, J=4.5, 1.5 Hz, 2H, pyridine H-3 & H-5), 8.14 (s, 1H, bromopyridine H-6), 8.52 (dd, J=4.4, 1.5 Hz, 2H, pyridine H-2 & H-6);

後処理

  1. customThis was prepared
  2. filtrationFiltration
  3. washwashing
  4. customas previously described gave the product (265 mg, 58% for two steps) as a yellow solid

出典と根拠

ORDレコード
ord-ba640213accc4416819c667c4b9a2497
出典データセット
uspto-grants-2012_01
特許番号
US08088761B2

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