Triethylamine → HCID 59534655, compound

HRID 1661715Notes

Reaction equation

HRID 1661715 reaction equation
[NH2:1][CH:2]([C:4]1[CH:5]=[C:6]([C:10]2[N:11]([CH3:22])[C:12]3[C:17]([C:18]=2[C:19]#[N:20])=[CH:16][CH:15]=[C:14]([Cl:21])[CH:13]=3)[CH:7]=[N:8][CH:9]=1)[CH3:3].[CH2:23]([S:25](Cl)(=[O:27])=[O:26])[CH3:24].C(N(CC)CC)C>ClCCl>[Cl:21][C:14]1[CH:13]=[C:12]2[C:17]([C:18]([C:19]#[N:20])=[C:10]([C:6]3[CH:5]=[C:4]([CH:2]([NH:1][S:25]([CH2:23][CH3:24])(=[O:27])=[O:26])[CH3:3])[CH:9]=[N:8][CH:7]=3)[N:11]2[CH3:22])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 58215676HCID 58215676, compound

Product 1

HCID 59534655HCID 59534655, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A flask is charged with 2-[5-(1-amino-ethyl)-pyridin-3-yl]-6-chloro-1-methyl-1H-indole-3-carbonitrile (0.072 g, 0.209 mmol) and dichloromethane (3 mL). Ethanesulfonyl chloride (0.060 g, 0.525 mmol) and triethylamine (0.059 mL, 0.417 mmol) are added and the reaction is stirred at room temperature overnight. The reaction mixture is concentrated in vacuo to give a residue which is purified by silica gel flash chromatography (heptane-ethyl acetate, 1:1) to afford ethanesulfonic acid {1-[5-(6-chloro-3-cyano-1-methyl-1H-indol-2-yl)-pyridin-3-yl]-ethyl}-amide as a white solid. 1H NMR (400 MHz, MeOD) δ ppm 1.32 (t, J=7.5 Hz, 3H), 1.65 (d, J=7.1 Hz, 3H), 2.96-3.15 (m, 2H), 3.84 (s, 3H), 4.75-4.86 (m, 1H), 7.39 (dd, J=8.6, 1.8 Hz, 1H), 7.73 (d, J=8.6 Hz, 1H), 7.78 (d, J=1.5 Hz, 1H), 8.20 (t, J=2.0 Hz, 1H), 8.80 (d, J=2.0 Hz, 1H), 8.83 (d, J=2.3 Hz, 1H). HRMS (ESI) m/z 403.1005 [(M+H)+ Calcd for C19H20N4O2SCl: 403.0996].

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customto give a residue which
  3. customis purified by silica gel flash chromatography (heptane-ethyl acetate, 1:1)

Sources & evidence

ORD record
ord-a39f8fed5ae04790ad07b873bd1ba350
Source dataset
uspto-grants-2011_10
Patent number
US08030334B2

Reaction notes

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