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 601331ノート

反応式

HRID 601331 の反応式
[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]

参加物

5

反応物 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

生成物 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)-one収率 66.1%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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)−.

後処理

  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

出典と根拠

ORDレコード
ord-8a179101ec3e41a8bc4bf361e06115a0
出典データセット
uspto-grants-2011_03
特許番号
US07902203B2

反応ノート

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