Water → N-(4-amino-5-cyano-6-isopropoxypyridin-2-yl)-2-(2,5-dimethoxyphenyl)acetamide

HRID 1364520

반응식

HRID 1364520 반응식
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH:11]([CH3:13])[CH3:12])[N:5]=[C:4]([NH2:14])[CH:3]=1.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=1[CH2:25][C:26](Cl)=[O:27].O>N1C=CC=CC=1.C(Cl)Cl>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH:11]([CH3:12])[CH3:13])[N:5]=[C:4]([NH:14][C:26](=[O:27])[CH2:25][C:18]2[CH:19]=[C:20]([O:23][CH3:24])[CH:21]=[CH:22][C:17]=2[O:16][CH3:15])[CH:3]=1

참가 물질

6

반응물 3

HCID 962WaterHCID 596088(2,5-Dimethoxyphenyl)acetyl chlorideHCID 11550144HCID 11550144, 화합물

생성물 1

HCID 11610382N-(4-amino-5-cyano-6-isopropoxypyridin-2-yl)-2-(2,5-dimethoxyphenyl)acetamide수율 47%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 100 mg (0.520 mmol) of 4,6-diamino-2-isopropoxy-nicotinonitrile in 1 mL of pyridine was added 3 mL of CH2Cl2 followed by a solution of 150 mg (0.699 mmol) of 2,5-dimethoxyphenylacetyl chloride (prepared from (2,5-dimethoxyphenyl)acetic acid and oxalyl chloride in CH2Cl2) in 1 mL of CH2Cl2. The mixture was stirred at ambient temperature for 10 minutes then 1 mL of water was added, and the mixture was concentrated under reduced pressure. The residue was taken up in 20 mL of warm ethyl acetate and extracted with water (1×5 mL), 1M HCl(aq.) (2×5 mL), saturated NaHCO3(aq.) (2×5 mL), and brine (1×5 mL), dried over MgSO4, filtered, and concentrated to a solid. Recrystallization from methanol or 2-propanol provided 90 mg (47%) of a white solid. 1H NMR (300 MHz, d6-DMSO) δ 10.06 (s, 1H), 7.10 (s, 1H), 6.90 (m, 1H), 6.84 (s, 2H), 6.79 (m, 2H), 5.28 (septet, 1H, J=6.1 Hz), 3.70 (s, 3H), 3.69 (s, 3H), 3.66 (s, 2H), 1.29 (d, 6H, J=6.1 Hz); MS (ESI) m/e=329 (M−Pr+H)+, 371 (M+H)+, 369 (M−H)−.

후처리

  1. concentrationthe mixture was concentrated under reduced pressure
  2. extractionextracted with water (1×5 mL), 1M HCl(aq.) (2×5 mL), saturated NaHCO3(aq.) (2×5 mL), and brine (1×5 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to a solid
  6. customRecrystallization from methanol or 2-propanol

출처 및 근거

ORD 기록
ord-66a564a8ea3a48edb761ff5ea9e8f107
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07888374B2

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