Pyridine → N-{4-[(5,5-Dioxido-2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,2,4]-benzothiadiazin-7-yl)oxy]benzyl}-N-methylmethanesulphonamide

HRID 29778Notes

Reaction equation

HRID 29778 reaction equation
[CH2:1]1[N:9]2[CH:4]([NH:5][S:6](=[O:16])(=[O:15])[C:7]3[CH:13]=[C:12]([OH:14])[CH:11]=[CH:10][C:8]=32)[CH2:3][CH2:2]1.[CH3:17][N:18]([CH2:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)[S:19]([CH3:22])(=[O:21])=[O:20].N1C=CC=CC=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[O:16]=[S:6]1(=[O:15])[C:7]2[CH:13]=[C:12]([O:14][C:27]3[CH:28]=[CH:29][C:24]([CH2:23][N:18]([CH3:17])[S:19]([CH3:22])(=[O:20])=[O:21])=[CH:25][CH:26]=3)[CH:11]=[CH:10][C:8]=2[N:9]2[CH2:1][CH2:2][CH2:3][CH:4]2[NH:5]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 98135182,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,2,4]benzothiadiazin-7-ol 5,5-dioxideHCID 69197336(4-{[Methyl(methylsulphonyl)amino]methyl}phenyl)boronic acid

Product 1

HCID 69198819N-{4-[(5,5-Dioxido-2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,2,4]-benzothiadiazin-7-yl)oxy]benzyl}-N-methylmethanesulphonamide

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension composed of 5.74 mg (3.37 mmol) of 2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,2,4 ]benzothiadiazin-7-ol 5,5-dioxide, 926 mg (4.04 mmol) of (4-{[methyl(methylsulphonyl)amino ]methyl}phenyl)boronic acid, 920 mg (5.06 mmol), of copper(II) acetate, 817 μl (10.10 mmol) of pyridine and about 4 g of 4 Å molecular sieve in 50 ml of CH2Cl2 is stirred overnight. The reaction mixture is filtered, rinsing with CH2Cl2/MeOH (1/1). The filtrate is concentrated and then directly placed on a silica column which is eluted with a CH2Cl2/MeOH 95/5 system. The fractions containing the expected product are combined and evaporated, and the residue is taken up in ethyl ether. After filtering off the solid, the title product is recovered in the form of white powder.

Workup

  1. filtrationThe reaction mixture is filtered
  2. washrinsing with CH2Cl2/MeOH (1/1)
  3. concentrationThe filtrate is concentrated
  4. washis eluted with a CH2Cl2/MeOH 95/5 system
  5. additionThe fractions containing the expected product
  6. customevaporated
  7. filtrationAfter filtering off the solid
  8. customthe title product is recovered in the form of white powder

Sources & evidence

ORD record
ord-745a8dcc8a824cbfac7babfbdefb67db
Source dataset
uspto-grants-2008_09
Patent number
US07423034B2

Reaction notes

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