Butyric Acid → 5-Butyramido-2-propylimidazo[4,5-b]pyridine

HRID 1029563

反応式

HRID 1029563 の反応式
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[C:4]([NH2:11])[N:3]=1.[C:12]([OH:17])(=O)[CH2:13][CH2:14][CH3:15].C(Cl)Cl>CO.O.[NH4+].[OH-].[Pd]>[C:12]([NH:11][C:4]1[N:3]=[C:2]2[N:1]=[C:4]([CH2:5][CH2:6][CH3:7])[NH:8][C:7]2=[CH:6][CH:5]=1)(=[O:17])[CH2:13][CH2:14][CH3:15]

参加物

8

反応物 3

HCID 264Butyric AcidHCID 6344DichloromethaneHCID 3199982,6-Diamino-3-nitropyridine

生成物 1

HCID 224073815-Butyramido-2-propylimidazo[4,5-b]pyridine収率 49.1%

試薬・触媒・溶媒 4

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 962Water溶媒HCID 14923Ammonium Hydroxide溶媒

反応条件

温度
80 °C

実験手順

A mixture of 2,6-diamino-3-nitropyridine (878 mg, 5.7 mmol) and Pd-C (10%, 100 mg) in MeOH (100 mL) was stirred under 1 atm. H2 for 16 hours. The mixture (containing the air sensitive triamine) was filtered, evaporated, and to this flask was added polyphosphoric acid (15 mL) and butyric acid (1.05 mL, 11.5 mmol). This mixture was heated to 80° C. for 5 hours, cooled to room temperature, diluted with water and neutralized with concentrated NH4OH. Extractive workup (CH2Cl2) gave 345 mg of 5-(butyramido)-2-propylimidazo[4,5-b]pyridine: 1H NMR (300 MHz, CDCl3) δ7.94 (d, 1H, J=8.5 Hz), 7.65 (d, 1H, J=8.5 Hz), 2.96 (t, 2H J=7.5 Hz), 2.30 (t, 2H J=7 Hz), 1.98-1.84 (m, 2H), 1.68-1.55 (m, 2H), 0.99 (t, 3H, J=7.5 Hz), 0.80 (t, 3H, J=7.0 Hz).

後処理

  1. filtrationwas filtered
  2. customevaporated
  3. temperaturecooled to room temperature

出典と根拠

ORDレコード
ord-4ed784dc78a24cd2938997a23c8937e8
出典データセット
uspto-grants-1992_04
特許番号
US05102880

関連ノート

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