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

HRID 1029563

반응식

HRID 1029563 반응식
[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]

참가 물질

8

반응물 3

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

생성물 1

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

시약·촉매·용매 4

HCID 23938Palladium촉매HCID 887Methanol용매HCID 962Water용매HCID 14923Ammonium Hydroxide용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-4ed784dc78a24cd2938997a23c8937e8
출처 데이터셋
uspto-grants-1992_04
특허 번호
US05102880

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