Hydrochloric Acid → HCID 59335136, compound

HRID 1510324Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([NH:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][C:17]([C:22](O)=[O:23])=[CH:16]3)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:25](N1C=CN=C1)([N:27]1C=CN=[CH:28]1)=O.CNC.Cl>O1CCCC1.C(OCC)(=O)C>[CH3:25][N:27]([CH3:28])[C:22]([C:17]1[NH:18][C:19]2[C:15]([CH:16]=1)=[CH:14][C:13]([NH:12][S:9]([C:4]1[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=1)(=[O:10])=[O:11])=[CH:21][CH:20]=2)=[O:23]

Participants

Conditions

Temperature: 40 °C

Procedure

110 mg 5-(3,5-dichloro-phenylsulphonylamino)-1H-indole-2-carboxylic acid are dissolved in 4 ml of tetrahydrofuran, combined with 51 mg carbonyldiimidazole and stirred for 3 hours at ambient temperature and for 1 hour at 40° C. After cooling to ambient temperature 600 μl of a 2 M solution of dimethylamine in tetrahydrofuran are added and the mixture is stirred overnight at ambient temperature. The solvent is eliminated in vacuo, the residue is divided between ethyl acetate and 0.5 N hydrochloric acid and the organic phase is washed with water and saturated sodium chloride solution. After drying with magnesium sulphate the solvent is eliminated in vacuo and the residue is chromatographed on silica gel (ethyl acetate).

Workup

additionare added
stirringthe mixture is stirred overnight at ambient temperature
washthe organic phase is washed with water and saturated sodium chloride solution
dry with materialAfter drying with magnesium sulphate the solvent
customthe residue is chromatographed on silica gel (ethyl acetate)

Sources & evidence

ORD record: ord-7a3dc01eb893424f8731991bc3b98e91
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08211923B2

Reaction notes

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