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Diisopropylethylamine → N-(1-{2-[3-(2-Methyl-quinolin-4-yl)-ureido]-ethyl}-piperidin-4-yl)-4-trifluoromethyl-benzenesulfonamide

HRID 2223692
Notes
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Reaction equation

HRID 2223692 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[NH2:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][NH:24][C:25]([NH:27][C:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[N:31]=[C:30]([CH3:38])[CH:29]=2)=[O:26])[CH2:18][CH2:17]1.CCN(C(C)C)C(C)C>C1COCC1>[CH3:38][C:30]1[CH:29]=[C:28]([NH:27][C:25](=[O:26])[NH:24][CH2:23][CH2:22][N:19]2[CH2:20][CH2:21][CH:16]([NH:15][S:9]([C:6]3[CH:7]=[CH:8][C:3]([C:2]([F:14])([F:13])[F:1])=[CH:4][CH:5]=3)(=[O:11])=[O:10])[CH2:17][CH2:18]2)[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27773994-(Trifluoromethyl)benzenesulfonyl chlorideHCID 597159051-[2-(4-Amino-piperidin-1-yl)-ethyl]-3-(2-methyl-quinolin-4-yl)-urea

Product 1

HCID 10289528N-(1-{2-[3-(2-Methyl-quinolin-4-yl)-ureido]-ethyl}-piperidin-4-yl)-4-trifluoromethyl-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Conditions

Temperature
40 °C

Procedure

A solution of 4-trifluoromethyl-benzenesulfonyl chloride (0.03 mmol) in THF (1 mL) is added to a mixture of 1-[2-(4-amino-piperidin-1-yl)-ethyl]-3-(2-methyl-quinolin-4-yl)-urea (0.025 mmol), DIPEA (6 μL) and THF (1 mL). The reaction mixture is heated at 40° C. for 18 h, and then is evaporated to dryness. The residue is taken up in formic acid (1 mL), and purified by preparative HPLC to provide the title compound.

Workup

  1. customis evaporated to dryness
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-92cd7b79463f42909f541a73e658acb5
Source dataset
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07375227B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes