Triethylamine → Ammonium Hydroxide

HRID 593645Notes

Reaction equation

HRID 593645 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.C(N(N[S:28](Cl)(=[O:30])=[O:29])CC)C.[CH2:32]([N:34](CC)[CH2:35][CH3:36])[CH3:33]>ClCCl>[NH4+:1].[OH-:29].[CH2:32]([N:34]([CH2:35][CH3:36])[S:28]([NH:1][CH2:2][C:3]1[CH:8]=[N:7][CH:6]=[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:4]=1)(=[O:30])=[O:29])[CH3:33]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 55280800HCID 55280800, compoundHCID 58215751HCID 58215751, compound

Product 2

HCID 14923Ammonium HydroxideYield 0.1%HCID 59534659HCID 59534659, 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 (Example 186e, 0.103 g, 0.349 mmol) and dichloromethane (2 mL). Diethylaminosulfamoyl chloride (0.072 g, 0.419 mmol) and triethylamine (0.100 mL, 0.699 mmol) are added and the reaction is stirred at room temperature overnight. The reaction mixture is concentrated in vacuo and the residue is purified by reverse phase HPLC with Xbridge Shield RP18 column and a 0.1% aqueous NH4OH in acetonitrile gradient to afford N,N-diethyl-N′-[5-(6-chloro-3-cyano-1-methyl-1H-indol-2-yl)-pyridin-3-ylmethyl]-sulfamide as a solid. 1H NMR (400 MHz, MeOD) δ ppm 1.20 (t, J=7.1 Hz, 6H), 3.30 (q, J=7.1 Hz, 4H), 3.83 (s, 3H), 4.35 (s, 2H), 7.38 (dd, J=8.6, 1.8 Hz, 1H), 7.71 (d, J=8.6 Hz, 1H), 7.77 (d, J=1.5 Hz, 1H), 8.17 (t, J=2.1 Hz, 1H), 8.79 (dd, J=3.7, 2.1 Hz, 2H). HRMS (ESI) m/z 432.1278 [(M+H)+ Calcd for C20H23ClN5O2S: 432.1261].

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-44c00f2e99ed4768b5b0a5207129d9ef
Source dataset
uspto-grants-2016_01
Patent number
US09242963B2

Reaction notes

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