Water → HCID 59843462, compound

HRID 2383274Notes

Reaction equation

HRID 2383274 reaction equation
[CH3:1][N:2]1[CH2:14][CH2:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([NH:15][S:16]([C:19]4[CH:24]=[CH:23][C:22]([NH:25]C(=O)C)=[CH:21][CH:20]=4)(=[O:18])=[O:17])[CH:10]=3)[NH:5][C:4]=2[CH2:3]1.[OH-].[Na+].O.CCOC(C)=O>CC(O)=O>[NH2:25][C:22]1[CH:23]=[CH:24][C:19]([S:16]([NH:15][C:9]2[CH:10]=[C:11]3[C:6](=[CH:7][CH:8]=2)[NH:5][C:4]2[CH2:3][N:2]([CH3:1])[CH2:14][CH2:13][C:12]3=2)(=[O:18])=[O:17])=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 59843475HCID 59843475, compound

Product 1

HCID 59843462HCID 59843462, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of N-[4-(2-Methyl-2,3,4,9-tetrahydro-1H-β-carbolin-6-ylsulfamoyl)-phenyl]-acetamide (example 7) (80 mg, 0.2 mmol) in 1 mL of an aqueous 10% de NaOH solution was refluxed for 2 h. The resulting mixture was treated with H2O (25 mL) and EtOAc (25 mL) and neutralized by addition of AcOH glacial. The aqueous phase was washed again with EtOAc and the combined organic extracts dried to afford 50 mg of 4-amino-N-(2-methyl-2,3,4,9-tetrahydro-1H-β-carbolin-6-yl)-benzenesulfonamide as a cream colored amorphous solid, mp 236-237° C. 1H-NMR (300 MHz, DMSO-d6): (ppm) 2.36 (s, 3H); 2.55 (bb, 2H); 2.61 (bb, 2H); 3.45 (bb, 2H); 5.83 (bb, 2H); 6.44 (sys AB, 2H, J=8.7 Hz); 6.68 (dd, 1H, J=8.4, 1.8 Hz); 6.99 (bb, 1H); 7.05 (d, 1H, J=8.4 Hz); 7.25 (sys AB, 2H, J=8.7 Hz); 9.27 (s, 1H); 10.63 (s, 1H).

Workup

  1. washThe aqueous phase was washed again with EtOAc
  2. customthe combined organic extracts dried

Sources & evidence

ORD record
ord-4d65edca7e91482fbf9662d08ae13849
Source dataset
uspto-grants-2012_09
Patent number
US08263609B2

Reaction notes

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