Potassium Carbonate → HCID 70343314, compound

HRID 583086Notes

Reaction equation

HRID 583086 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]3[CH2:15][CH2:14][NH:13][CH2:12]3)=[CH:7][NH:8]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:23][CH2:24][N:25]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[CH2:28][N:27]([CH:35]([CH3:37])[CH3:36])[S:26]1(=[O:39])=[O:38]>O.C(OCC)(=O)C>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]3[CH2:15][CH2:14][N:13]([CH2:23][CH2:24][N:25]4[C:30]5[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=5[CH2:28][N:27]([CH:35]([CH3:36])[CH3:37])[S:26]4(=[O:39])=[O:38])[CH2:12]3)=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 17777147HCID 17777147, compoundHCID 17777152HCID 17777152, compound

Product 1

HCID 70343314HCID 70343314, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-{6-Fluoro-indol-3-yl}-pyrrolidine (500 mg, 2.45 mmol), potassium carbonate (1.04 g, 9.8 mmol), and 1-(2-chloroethyl)-3,4-dihydro-3-(1-methylethyl)-1H-2,1,3-benzothiadiazine-2,2-dioxide (708 mg, 2.45 mmol) were refluxed in water (15 ml) under nitrogen overnight. The solid was dissolved in ethyl acetate(2×100 ml) and washed with brine, dried, filtered and evaporated in vacuo to afford a brown oil. Column chromatography eluting with ethyl acetate gave a yellow solid, 3,4-dihydro-1-{2-[3-(6-fluoroindol-3-yl)-pyrrolidinyl]-1-ethyl}-3-(1-methylethyl)-1H-2,1,3-benzothiadiazine-2,2-dioxide, m.p.50.8-54.4° C.

Workup

  1. washwashed with brine
  2. customdried
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customto afford a brown oil
  6. washColumn chromatography eluting with ethyl acetate

Sources & evidence

ORD record
ord-3c8cb47f9f69487da987d4da028b846e
Source dataset
uspto-grants-1999_07
Patent number
US05929072

Reaction notes

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