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 601331Notes

Reaction equation

HRID 601331 reaction equation
[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]

Participants

5

Reactant 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

Product 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)-oneYield 66.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

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)−.

Workup

  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

Sources & evidence

ORD record
ord-8a179101ec3e41a8bc4bf361e06115a0
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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