N-methylcyclopentanamine → HCID 86686119, compound

HRID 409731Notes

Reaction equation

C[O:2][C:3](=[O:24])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][N:20]=[C:19](Cl)[N:18]=3)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1.[CH3:25][NH:26][CH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1>C(#N)C>[CH:27]1([N:26]([CH3:25])[C:19]2[N:18]=[C:17]([N:14]3[CH2:15][CH2:16][CH:11]([C:8]4[CH:7]=[CH:6][C:5]([CH2:4][C:3]([OH:2])=[O:24])=[CH:10][CH:9]=4)[CH2:12][CH2:13]3)[CH:22]=[CH:21][N:20]=2)[CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

Conditions

Temperature: 150 °C

Procedure

To 2.70 g (7.81 mmol) {4-[1-(2-chloro-pyrimidin-4-yl)-piperidin-4-yl]-phenyl}-acetic acid methyl ester (XII.2) in 20 mL ACN are added 2.64 mL (23.4 mmol) N-methyl-cyclopentylamine. The mixture is stirred for 2 h at 150° C. under microwave irradiation. After that time, the solvent is evaporated, the residue taken up in 60 mL ethanol and 30 mL 1N NaOH are added. The mixture is stirred for 1 h at rt and for 1 h at 40° C. Subsequently, 30 mL 1N HCl are added, the mixture is concentrated in vacuo and extracted with DCM. The organic layer is dried over sodium sulphate and the solvent is evaporated. The residue is purified by column chromatography (silica gel; DCM:EtOH 80:20) to yield the desired product.

Workup

customAfter that time, the solvent is evaporated
addition30 mL 1N NaOH are added
stirringThe mixture is stirred for 1 h at rt and for 1 h at 40° C
additionSubsequently, 30 mL 1N HCl are added
concentrationthe mixture is concentrated in vacuo
extractionextracted with DCM
dry with materialThe organic layer is dried over sodium sulphate
customthe solvent is evaporated
customThe residue is purified by column chromatography (silica gel; DCM:EtOH 80:20)

Sources & evidence

ORD record: ord-bc29bb57ef984389ad434410e51bee1a
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759528B2

Reaction notes

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