Diisopropylethylamine → HCID 71542094, compound

HRID 1850231Notes

Reaction equation

HRID 1850231 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])[C:23]([F:35])=[CH:22][N:21]=1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[F:35][C:23]1[C:24]([N:26]2[C@@H:30]([CH:31]([CH3:32])[CH3:33])[CH2:29][O:28][C:27]2=[O:34])=[N:25][C:20]([NH:1][C@H:2]([C:4]2[CH:9]=[CH:8][C:7]([C:10]([N:12]3[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]3)=[O:11])=[C:6]([F:18])[CH:5]=2)[CH3:3])=[N:21][CH:22]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 86730285HCID 86730285, compoundHCID 86730286HCID 86730286, compound

Product 1

HCID 71542094HCID 71542094, compoundYield 12.5%

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-chloro-5-fluoropyrimidin-4-yl)-4-isopropyloxazolidin-2-one (0.030 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 8 hours or until done by LCMS. The reaction was let cool, 0.5 ml of NMP added, filtered, purified by prep LC and lyophilized to give 4.5 mg of (S)-3-(5-fluoro-2-((S)-1-(3-fluoro-4-(piperidine-1-carbonyl)phenyl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-one as TFA Salt. LCMS m/z 474.2 (M+H)+, Rt 0.91 min.

Workup

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

Sources & evidence

ORD record
ord-1b11ff58506441f0a3f9f3dfe7b48a07
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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