Diisopropylethylamine → {1-[4-(4-Cyano-3-fluoro-phenyl)-5-(4-methoxy-phenyl)-6-oxo-1,6-dihydro-pyrimidin-2-yl]-piperidin-4-yl}-carbamic acid tert-butyl ester

HRID 1773364Notes

Reaction equation

HRID 1773364 reaction equation
CO[C:3](=[O:24])[CH:4]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)[C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[C:9]([F:15])[CH:8]=1)=O.[C:25]([O:29][C:30](=[O:41])[NH:31][CH:32]1[CH2:37][CH2:36][N:35]([C:38](=[NH:40])[NH2:39])[CH2:34][CH2:33]1)([CH3:28])([CH3:27])[CH3:26].CCN(C(C)C)C(C)C>C1(C)C=CC=CC=1>[C:25]([O:29][C:30](=[O:41])[NH:31][CH:32]1[CH2:33][CH2:34][N:35]([C:38]2[NH:40][C:3](=[O:24])[C:4]([C:16]3[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=3)=[C:5]([C:7]3[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[C:9]([F:15])[CH:8]=3)[N:39]=2)[CH2:36][CH2:37]1)([CH3:28])([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 72206806(1-Carbamimidoyl-piperidin-4-yl)-carbamic acid tert-butyl esterHCID 1184831003-(4-Cyano-3-fluoro-phenyl)-2-(4-methoxy-phenyl)-3-oxo-propionic acid methyl ester

Product 1

HCID 136994852{1-[4-(4-Cyano-3-fluoro-phenyl)-5-(4-methoxy-phenyl)-6-oxo-1,6-dihydro-pyrimidin-2-yl]-piperidin-4-yl}-carbamic acid tert-butyl esterYield 4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-(4-cyano-3-fluoro-phenyl)-2-(4-methoxy-phenyl)-3-oxo-propionic acid methyl ester (1.8 g, 5.5 mmol), (1-carbamimidoyl-piperidin-4-yl)-carbamic acid tert-butyl ester (2.6 g, 9.2 mmol), DIEA (2.4 g, 18.3 mmol) in toluene (50 mL) was refluxed overnight. The solvent was concentrated in vacuo. The residue was suspended in MeOH and the solids were filtered to give 100 mg (4%) of the title compound. [M+H] Calc'd for C28H30FN5O4, 520. Found, 520.

Workup

  1. temperaturewas refluxed overnight
  2. concentrationThe solvent was concentrated in vacuo
  3. filtrationthe solids were filtered

Sources & evidence

ORD record
ord-941326a5528d417d9af5e805f042bc2c
Source dataset
uspto-grants-2016_02
Patent number
US09255097B2

Reaction notes

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