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Diisopropylethylamine → HCID 86730284, compound

HRID 1850230
Notes
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Reaction equation

HRID 1850230 reaction equation
[NH2:1][C@H:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])=[C:6]([F:18])[CH:5]=1)[CH3:3].Cl[C:20]1[N:25]=[C:24]([N:26]2[C@@H:30]([CH:31]([CH3:33])[CH3:32])[CH2:29][O:28][C:27]2=[O:34])[CH:23]=[CH:22][N:21]=1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[F:18][C:6]1[CH:5]=[C:4]([C@@H:2]([NH:1][C:20]2[N:25]=[C:24]([N:26]3[C@@H:30]([CH:31]([CH3:32])[CH3:33])[CH2:29][O:28][C:27]3=[O:34])[CH:23]=[CH:22][N:21]=2)[CH3:3])[CH:9]=[CH:8][C:7]=1[C:10]([N:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1)=[O:11]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 86730167(S)-3-(2-chloropyrimidin-4-yl)-4-isopropyloxazolidin-2-oneHCID 86730285HCID 86730285, compound

Product 1

HCID 86730284HCID 86730284, compoundYield 11.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Conditions

Temperature
107.5 °C

Procedure

To (S)-(4-(1-aminoethyl)-2-fluorophenyl)(piperidin-1-yl)methanone (0.019 g, 0.076 mmol) was added (S)-3-(2-chloropyrimidin-4-yl)-4-isopropyloxazolidin-2-one (0.028 g, 0.114 mmol), NMP (0.5 ml) and Hunig's Base (0.033 ml, 0.190 mmol). The reaction was heated at 105-110° C. for 16 hours or until done by LCMS. The reaction was let cool, 0.5 ml of NMP was added, filtered, purified by prep LC and lyophilized to give 4.0 mg of (S)-3-(2-((S)-1-(3-fluoro-4-(piperidine-1-carbonyl)phenyl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-one as TFA Salt. LCMS m/z 456.1 (M+H)+, rt 0.74 min.

Workup

  1. temperatureThe reaction was let cool
  2. filtrationfiltered
  3. custompurified by prep LC

Sources & evidence

ORD record
ord-f227c62e09b947318dc97d6609bce05f
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08957068B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes