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

HRID 1630949Notes

Reaction equation

HRID 1630949 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-d78fc4d6bf804a419857cf93b63090aa
Source dataset
uspto-grants-2014_07
Patent number
US08791141B2

Reaction notes

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