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

HRID 855531Notes

Reaction equation

HRID 855531 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][S:18]([NH:21][C:22]1([C:25]2[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=2)[CH2:24][CH2:23]1)(=[O:20])=[O:19].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:28]3[CH:27]=[CH:26][C:25]([C:22]4([NH:21][S:18]([CH3:17])(=[O:19])=[O:20])[CH2:24][CH2:23]4)=[CH:30][CH:29]=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 69516977(4-{1-[(Methylsulphonyl)amino]cyclopropyl}phenyl)boronic acid

Product 1

HCID 11662366N-(1-{4-[(5,5-Dioxido-2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,2,4]benzothiadiazin-7-yl)oxy]phenyl}cyclopropyl)methanesulphonamide

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension composed of 290 mg (1.21 mmol) of 2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,2,4]benzothiadiazin-7-ol 5,5-dioxide, 465 mg (1.82 mmol) of the compound obtained in Step D, 330 mg (1.82 mmol) of copper(II) acetate, 294 μl (3.64 mmol) of pyridine and about 3.5 g of 4 Å molecular sieve in 35 ml of CH2Cl2 is stirred for 5 hours at ambient temperature. The reaction mixture is filtered and rinsed with CH2Cl2/MeOH (1/1). The filtrate is concentrated and then directly applied to a silica column, eluting with a mixture of CH2Cl2/acetone 96/4. The fractions containing the expected compound are collected and evaporated and the residue is taken up in a small amount of ethyl ether. After filtering off the solid, the title compound is collected in the form of a white powder.

Workup

  1. filtrationThe reaction mixture is filtered
  2. washrinsed with CH2Cl2/MeOH (1/1)
  3. concentrationThe filtrate is concentrated
  4. washeluting with a mixture of CH2Cl2/acetone 96/4
  5. additionThe fractions containing the expected compound
  6. customare collected
  7. customevaporated
  8. filtrationAfter filtering off the solid
  9. customthe title compound is collected in the form of a white powder

Sources & evidence

ORD record
ord-f6e3de28668b42f081848e65370d73e9
Source dataset
uspto-grants-2007_08
Patent number
US07262190B2

Reaction notes

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