Toluene → HCID 86711155, compound

HRID 625181Notes

Reaction equation

HRID 625181 reaction equation
Cl[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([C:13]([NH2:15])=[O:14])=[CH:12][C:7]=2[S:6][C:5]2[CH:16]=[CH:17][CH:18]=[CH:19][C:4]=2[N:3]=1.C1(C)C=CC=CC=1.[N:27]1([CH2:33][CH2:34][O:35][CH2:36][CH2:37][OH:38])[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>CN(C=O)C>[OH:38][CH2:37][CH2:36][O:35][CH2:34][CH2:33][N:27]1[CH2:32][CH2:31][N:30]([C:2]2[C:8]3[CH:9]=[CH:10][C:11]([C:13]([NH2:15])=[O:14])=[CH:12][C:7]=3[S:6][C:5]3[CH:16]=[CH:17][CH:18]=[CH:19][C:4]=3[N:3]=2)[CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 1394361-[2-(2-Hydroxyethoxy)ethyl]piperazineHCID 86711153HCID 86711153, compound

Product 1

HCID 86711155HCID 86711155, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 11-chloro-dibenzo[b,f][1,4]thiazepine-3-carboxylic acid amide, prepared as described in the previous step, (0.40 g) in DMF (1.5 mL) and toluene (1.5 mL) was added 2-(2-piperazin-1-yl-ethoxy)-ethanol (0.50 g, 2.9 mmol). The solution was heated in a 110° C. oil bath under nitrogen for 5 hours, concentrated, and purified (silica gel, 2-5% methanol-dichloromethane containing ammonia eluent) to give the title compound as an off white solid. LC-MS: m/z 427 (M+1).

Workup

  1. concentrationconcentrated
  2. custompurified
  3. addition(silica gel, 2-5% methanol-dichloromethane containing ammonia eluent)

Sources & evidence

ORD record
ord-c1fb51c7072f4d28a78a04e74c217f97
Source dataset
uspto-grants-2016_04
Patent number
US09304126B2

Reaction notes

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