Potassium Carbonate → HCID 178526673、化合物

HRID 895663ノート

反応式

HRID 895663 の反応式
Cl.Cl.[NH:3]1[C:11]2[CH2:10][CH2:9][NH:8][CH2:7][C:6]=2[N:5]=[CH:4]1.Cl[C:13]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][N:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N+:19]([C:18]1[C:13]([N:8]2[CH2:9][CH2:10][C:11]3[NH:3][CH:4]=[N:5][C:6]=3[CH2:7]2)=[N:14][CH:15]=[CH:16][CH:17]=1)([O-:21])=[O:20]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 796132-Chloro-3-nitropyridineHCID 164180044,5,6,7-Tetrahydro-3H-imidazo[4,5-c]pyridine--hydrogen chloride (1/2)

生成物 1

HCID 178526673HCID 178526673、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride (2.0 g, 12.5 mmol; prepared essentially as described by Habermehl, E., Heterocycles 5:127,133 (1976)), 2-chloro-3-nitropyridine (1.7 g, 11.25 mmol) and K2CO3 (5.2 g, 37.5 mmol) in 25 mL of DMF is heated at 50° C. for 4 hours and then allowed to cool to room temperature. The mixture is then partitioned between ethyl acetate and water and the layers are separated. The aqueous layer is then further extracted with ethyl acetate and the combined organic extracts are dried over Na2SO4, filtered and the solvents removed under reduced pressure. Column chromatography of the residue on silica gel (5% MeOH in CH2Cl2 as eluent) gives 5-(3-nitro-pyridin-2-yl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine as a yellow solid (1.5 g). 1H NMR δ (CDCl3): 8.34 (d, 1H), 8.16 (dd, 1H), 7.53(s, 1H), 6.74 (q, 1H), 4.31 (s, 2H), 3.94(t, 2H) and 2.91(t, 2H). MS: 246.3 (m+1).

後処理

  1. customprepared essentially
  2. customThe mixture is then partitioned between ethyl acetate and water
  3. customthe layers are separated
  4. extractionThe aqueous layer is then further extracted with ethyl acetate
  5. dry with materialthe combined organic extracts are dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvents removed under reduced pressure

出典と根拠

ORDレコード
ord-2709eb236d904e1ea4c490b69cbe68cd
出典データセット
uspto-grants-2005_07
特許番号
US06916827B2

反応ノート

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