Triethylamine → [(E)-1-[3-[(7-fluoroquinolin-6-yl)-hydroxymethyl]imidazo[1,2-b]pyridazin-6-yl]ethylideneamino]urea

HRID 456082노트

반응식

HRID 456082 반응식
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH:12]([OH:25])[C:13]1[N:17]2[N:18]=[C:19]([C:22](=O)[CH3:23])[CH:20]=[CH:21][C:16]2=[N:15][CH:14]=1.Cl.[NH2:27][NH:28][C:29]([NH2:31])=[O:30].C(N(CC)CC)C>CO>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH:12]([OH:25])[C:13]1[N:17]2[N:18]=[C:19](/[C:22](=[N:27]/[NH:28][C:29]([NH2:31])=[O:30])/[CH3:23])[CH:20]=[CH:21][C:16]2=[N:15][CH:14]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 11236Semicarbazide hydrochlorideHCID 669270891-(3-((7-Fluoroquinolin-6-yl)(hydroxy)methyl)imidazo[1,2-b]pyridazin-6-yl)ethanone

생성물 1

HCID 71699884[(E)-1-[3-[(7-fluoroquinolin-6-yl)-hydroxymethyl]imidazo[1,2-b]pyridazin-6-yl]ethylideneamino]urea수율 47.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 1-(3-((7-fluoroquinolin-6-yl)(hydroxy)methyl)imidazo[1,2-b]pyridazin-6-yl)ethanone (100 mg, 0.27 mmol) in methanol (15 mL) was added semicarbazide hydrochloride (45 mg, 0.41 mmol). Triethyl amine was added dropwise to adjust the pH to 5-6. The reaction mixture was stirred at room temperature overnight. The precipitate was collected by filtration and dried over vacuum pump to afford 50 mg (yield: 47%) title compound as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.68 (s, 1H), 8.89 (dd, 1H), 8.45 (d, 1H), 8.25 (m, 2H), 7.99 (d, 1H), 7.72 (d, 1H), 7.57 (s, 1H), 7.52 (q, 1H), 6.67 (b, 2H), 6.62 (s, 1H), 6.47 (b, 1H), 2.19 (s, 3H). LCMS (method A): [MH]+=394, tR=3.95 min.

후처리

  1. filtrationThe precipitate was collected by filtration
  2. customdried over vacuum pump

출처 및 근거

ORD 기록
ord-bf399b70f4034a34ad6300e98ad17bc8
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497368B2

반응 노트

불러오는 중…