Potassium Carbonate → HCID 58107404, compound

HRID 873667Notes

Reaction equation

HRID 873667 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:40][CH2:39][C:9]2[N:10](S(C3C=CC=CC=3)(=O)=O)[C:11]3[CH:12]=[CH:13][C:14]([C:17](=[O:29])[C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([S:25](=[O:28])(=[O:27])[NH2:26])[CH:19]=4)=[CH:15][C:16]=3[C:8]=2[CH2:7]1)=[O:5])[CH3:2].C(OC(N1CCC2N(S(C3C=CC=CC=3)(=O)=O)C3C=C(C(=O)C4C=CC(Cl)=C(S(=O)(=O)N)C=4)C=CC=3C=2C1)=O)C.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1CO.O>[CH2:1]([O:3][C:4]([N:6]1[CH2:40][CH2:39][C:9]2[NH:10][C:11]3[CH:12]=[CH:13][C:14]([C:17](=[O:29])[C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([S:25](=[O:28])(=[O:27])[NH2:26])[CH:19]=4)=[CH:15][C:16]=3[C:8]=2[CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 66850720HCID 66850720, compoundHCID 66851051HCID 66851051, compound

Product 1

HCID 58107404HCID 58107404, compound

Reagents, catalysts & solvents 1

HCID 66577907Tetrahydrofuran-methanol waterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 5-benzenesulfonyl-8-(4-chloro-3-sulfamoyl-benzoyl)-1,3,4,5-tetrahydro-pyrido[4,3-b]indole-2-carboxylic acid ethyl ester and 5-benzenesulfonyl-7-(4-chloro-3-sulfamoyl-benzoyl)-1,3,4,5-tetrahydro-pyrido[4,3-b]indole-2-carboxylic acid ethyl ester (1 g) is dissolved in 5 mL of tetrahydrofuran-methanol-water (10:10:1) and treated with 0.344 g of potassium carbonate. The reaction mixture is heated at 140° C. for 15 min (microwave irradiation), filtered and concentrated. The residue is purified on reverse phase HPLC to give pure 8-(4-chloro-3-sulfamoyl-benzoyl)-1,3,4,5-tetrahydro-pyrido[4,3-b]indole-2-carboxylic acid ethyl ester MS (m/z): 462 (M+1); and 7-(4-chloro-3-sulfamoyl-benzoyl)-1,3,4,5-tetrahydro-pyrido[4,3-b]indole-2-carboxylic acid ethyl ester MS (m/z): 462 (M+1); both as yellow syrups. Both isomers are separated by HPLC (Chiracel OD-H 250-4.6 mm, flow 1 ml/Min, UV 235 nM, gradient hexane-ethanol 70-30). The retention times are 6.91 min for 8-(4-chloro-3-sulfamoyl-benzoyl)-1,3,4,5-tetrahydro-pyrido[4,3-b]indole-2-carboxylic acid ethyl ester and 10.20 min for 7-(4-chloro-3-sulfamoyl-benzoyl)-1,3,4,5-tetrahydro-pyrido[4,3-b]indole-2-carboxylic acid ethyl ester.

Workup

  1. custom(microwave irradiation)
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue is purified on reverse phase HPLC

Sources & evidence

ORD record
ord-b60cc705c01c4858818dc58cb9e7334e
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

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