Methylhydrazine → 1-amino-4-hydroxy-3-{7-[(methoxymethoxy)methyl]-1,1-dioxido-4H-thieno[2,3-e][1,2,4]thiadiazin-3-yl}quinolin-2(1H)-one

HRID 601331노트

반응식

HRID 601331 반응식
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([N:12]2C(=O)C3C(=CC=CC=3)C2=O)[C:4](=[O:23])[C:3]=1[C:24]1[NH:29][C:28]2[S:30][CH:31]=[C:32]([CH2:33][O:34][CH2:35][O:36][CH3:37])[C:27]=2[S:26](=[O:39])(=[O:38])[N:25]=1.CNN.C(N(CC)CC)C>O1CCOCC1>[NH2:12][N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([OH:1])=[C:3]([C:24]2[NH:29][C:28]3[S:30][CH:31]=[C:32]([CH2:33][O:34][CH2:35][O:36][CH3:37])[C:27]=3[S:26](=[O:39])(=[O:38])[N:25]=2)[C:4]1=[O:23]

참가 물질

5

반응물 3

HCID 6061MethylhydrazineHCID 8471TriethylamineHCID 1363584122-[4-hydroxy-3-{7-[(methoxymethoxy)methyl]-1,1-dioxido-4H-thieno[2,3-e][1,2,4]thiadiazin-3-yl}-2-oxoquinolin-1(2H)-yl]-1H-isoindole-1,3(2H)-dione

생성물 1

HCID 1363584111-amino-4-hydroxy-3-{7-[(methoxymethoxy)methyl]-1,1-dioxido-4H-thieno[2,3-e][1,2,4]thiadiazin-3-yl}quinolin-2(1H)-one수율 66.1%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

A solution of the product of Example 350D (185 mg, 0.326 mmol), methylhydrazine (43.47 μL, 2.5 equivalents), and triethylamine (0.126 mL, 3 equivalents) in 1,4-dioxane (10 mL) was heated at 102° C. for 3 hours. The reaction was concentrated under reduced pressure, and treated with a solution of methanol (75 mL) and 1N hydrochloric acid (100 mL). The resulting precipitate was collected by filtration and washed with water and diethyl ether to give the title compound as a white solid (94 mg, 66%). 1H NMR (300 MHz, DMSO-d6) δ 4.65 (s, 2 H), 4.71 (s, 2 H), 5.84 (br.s, 1 H), 7.44 (m, 2 H), 7.88 (m, 1 H), 8.04 (d, 1 H), 8.15 (d, 1 H), 14.73 (br.s, 2 H). MS (ESI−) m/z 435 (M−H)−.

후처리

  1. concentrationThe reaction was concentrated under reduced pressure
  2. additiontreated with a solution of methanol (75 mL) and 1N hydrochloric acid (100 mL)
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with water and diethyl ether

출처 및 근거

ORD 기록
ord-8a179101ec3e41a8bc4bf361e06115a0
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902203B2

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