Triethylamine → diethyl-sulfamic acid 5-(1-methyl-1H-indol-2-yl)-pyridin-3-yl-amide

HRID 593679Notes

Reaction equation

HRID 593679 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]([CH3:17])[C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:5]=[N:6][CH:7]=1.CN(C)[S:20](Cl)(=[O:22])=[O:21].[CH2:25]([N:27](CC)[CH2:28][CH3:29])[CH3:26]>ClCCl>[CH3:17][N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:16]=[C:8]1[C:4]1[CH:3]=[C:2]([NH:1][S:20](=[O:22])(=[O:21])[N:27]([CH2:28][CH3:29])[CH2:25][CH3:26])[CH:7]=[N:6][CH:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 582155792-(5-amino-pyridin-3-yl)-1-methyl-1H-indole

Product 1

HCID 67093275diethyl-sulfamic acid 5-(1-methyl-1H-indol-2-yl)-pyridin-3-yl-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(5-amino-pyridin-3-yl)-1-methyl-1H-indole (Example 100, 60 mg, 0.269 mmol) and dimethylsulfamoyl chloride (58 mg, 0.403 mmol) in dichloromethane (1 mL) is added triethylamine (54 mg, 0.537 mmol). After overnight stirring, the mixture is concentrated and purified by silica gel flash chromatography (heptane-ethyl acetate, 3:7) to give diethyl-sulfamic acid 5-(1-methyl-1H-indol-2-yl)-pyridin-3-yl-amide. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.77 (s, 6H), 3.76 (s, 3H), 6.89 (s, 1H), 7.07-7.12 (m, 1H), 7.20-7.25 (m, 1H), 7.53 (d, J=8.3 Hz, 1H), 7.61 (d, J=7.8 Hz, 1H), 7.75 (t, J=2.1 Hz, 1H), 8.46 (d, J=2.5 Hz, 1H), 8.52 (d, J=2.0 Hz, 1H). HRMS: (ESI) m/z 331.1226 [(M+H)+ Calcd for C16H18N4O2S 331.1223].

Workup

  1. concentrationthe mixture is concentrated
  2. custompurified by silica gel flash chromatography (heptane-ethyl acetate, 3:7)

Sources & evidence

ORD record
ord-ec8c29f2970746c3be0480ce8ac6e6a5
Source dataset
uspto-grants-2016_01
Patent number
US09242963B2

Reaction notes

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