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Morpholine → N-(3-chloro-4-fluorophenyl)-4-(3-morpholin-4-ylpropyl)-1,2,5-oxadiazole-3-carboxamide

HRID 2097661
Notes
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Reaction equation

HRID 2097661 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][C:9]1[C:13]([C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[C:19]([Cl:24])[CH:18]=2)=[O:15])=[N:12][O:11][N:10]=1)(=O)=O.CCN(C(C)C)C(C)C.[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1>C(#N)C>[Cl:24][C:19]1[CH:18]=[C:17]([NH:16][C:14]([C:13]2[C:9]([CH2:8][CH2:7][CH2:6][N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[N:10][O:11][N:12]=2)=[O:15])[CH:22]=[CH:21][C:20]=1[F:23]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 589417693-(4-[(3-Chloro-4-fluorophenyl)amino]carbonyl-1,2,5-oxadiazol-3-yl)propyl methanesulfonate

Product 1

HCID 58941763N-(3-chloro-4-fluorophenyl)-4-(3-morpholin-4-ylpropyl)-1,2,5-oxadiazole-3-carboxamideYield 54.2%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Conditions

Temperature
70 °C

Procedure

3-(4-[(3-Chloro-4-fluorophenyl)amino]carbonyl-1,2,5-oxadiazol-3-yl)propyl methanesulfonate (19 mg, 0.051 mmol) was dissolved in anhydrous ACN (100 μL,) followed by the addition of DIPEA (44 μL, 0.26 mmol) and morpholine (6.7 μL, 76.8 μmol). The reaction were stirred and heated at 70° C. for 3 h. The reaction was concentrated and purified by silica gel chromatography (60-100% ethyl acetate/hexanes) to give the desired product (10.2 mg, 54%). LCMS for C16H19ClFN4O3 (M+H)+: m/z=369.1.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by silica gel chromatography (60-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-c86047365c1a4990a227ed52aeb24f7a
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08450351B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes