Sodium hydride → N-(4-(4-(5-(cyclopentyloxy)pyridin-2-yloxy)phenyl)butan-2-yl)acetamide

HRID 1260502Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH:10]([NH:12][C:13](=[O:15])[CH3:14])[CH3:11])=[CH:4][CH:3]=1.Cl[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)=[CH:19][N:18]=1.[H-].[Na+]>CN1CCCC1=O>[CH:24]1([O:23][C:20]2[CH:21]=[CH:22][C:17]([O:1][C:2]3[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH:10]([NH:12][C:13](=[O:15])[CH3:14])[CH3:11])=[CH:6][CH:7]=3)=[N:18][CH:19]=2)[CH2:25][CH2:26][CH2:27][CH2:28]1

Participants

Conditions

Temperature: 240 °C

Procedure

N-[3-(4-Hydroxyphenyl)-1-methylpropyl]acetamide (104.9 mg, 0.51 mmol), 2-chloro-5-cyclopentyloxypyridine (100 mg, 0.51 mmol) and sodium hydride (50% in oil) (26 mg, 0.54 mmol) were treated at 230° C. in 5 ml of N-methylpyrrolidinone in a microwave reactor for 1 h. Addition of a further 26 mg of sodium hydride was followed by again heating at 240° C. for 1 h. The reaction mixture was concentrated, and the residue was taken up in ethyl acetate and water. The organic phase was separated off, concentrated and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 16 mg (9%), M+H+: 369.17.

Workup

concentrationThe reaction mixture was concentrated
customThe organic phase was separated off
concentrationconcentrated
custompurified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record: ord-e918a5028ec645a193a2c1dba799b3a6
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08470841B2

Reaction notes

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