Triethylamine → Ammonium Hydroxide

HRID 1661686Notes

Reaction equation

HRID 1661686 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[N:10]([CH3:21])[C:11]3[C:16]([C:17]=2[C:18]#[N:19])=[CH:15][CH:14]=[C:13]([Cl:20])[CH:12]=3)[CH:6]=[N:7][CH:8]=1.[CH:22]([S:25](Cl)(=[O:27])=[O:26])([CH3:24])[CH3:23].C(N(CC)CC)C>ClCCl>[NH4+:1].[OH-:26].[Cl:20][C:13]1[CH:12]=[C:11]2[C:16]([C:17]([C:18]#[N:19])=[C:9]([C:5]3[CH:4]=[C:3]([CH2:2][NH:1][S:25]([CH:22]([CH3:24])[CH3:23])(=[O:27])=[O:26])[CH:8]=[N:7][CH:6]=3)[N:10]2[CH3:21])=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 824082-Propanesulfonyl chlorideHCID 58215751HCID 58215751, compound

Product 2

HCID 14923Ammonium HydroxideYield 0.1%HCID 59534634HCID 59534634, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A flask is charged with 2-(5-aminomethyl-pyridin-3-yl)-6-chloro-1-methyl-1H-indole-3-carbonitrile (0.075 g, 0.253 mmol) and dichloromethane (2 mL). Isopropylsulfonyl chloride (0.031 mL, 0.278 mmol) and triethylamine (0.071 mL, 0.506 mmol) are added and the reaction is stirred at room temperature overnight. The reaction mixture is concentrated in vacuo. The residue is purified by reverse phase HPLC with Xbridge Shield RP18 column and a 0.1% aqueous NH4OH in acetonitrile gradient to afford propane-2-sulfonic acid [5-(6-chloro-3-cyano-1-methyl-1H-indol-2-yl)-pyridin-3-ylmethyl]-amide as a solid. 1H NMR (400 MHz, MeOD) δ ppm 1.40 (d, J=6.8 Hz, 6H), 3.25-3.32 (m, 1H), 3.84 (s, 3H), 4.50 (s, 2H), 7.38 (dd, J=8.6, 1.8 Hz, 1H), 7.72 (d, J=8.6 Hz, 1H), 7.77 (d, J=1.5 Hz, 1H), 8.18 (t, J=2.0 Hz, 1H), 8.81 (t, J=1.9 Hz, 2H). HRMS (ESI) m/z 403.0997 [(M+H)+ Calcd for C19H20ClN4O2S: 403.0996].

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customThe residue is purified by reverse phase HPLC with Xbridge Shield RP18 column

Sources & evidence

ORD record
ord-6de80b46519045ccaf441cf7e960d5fe
Source dataset
uspto-grants-2011_10
Patent number
US08030334B2

Reaction notes

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