Ethyl Acetate → N-(4-(4-(6-isopropoxypyridazin-3-yloxy)phenyl)butan-2-yl)acetamide

HRID 1260550Notes

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.[H-].[Na+].Cl[C:19]1[N:20]=[N:21][C:22]([O:25][CH:26]([CH3:28])[CH3:27])=[CH:23][CH:24]=1.C(OCC)(=O)C>CN1C(=O)CCC1.O>[CH:26]([O:25][C:22]1[N:21]=[N:20][C:19]([O:1][C:2]2[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]=2)=[CH:24][CH:23]=1)([CH3:28])[CH3:27]

Participants

Conditions

Temperature: 150 °C

Procedure

N-[3-(4-Hydroxyphenyl)-1-methylpropyl]acetamide (311 mg, 1.5 mmol) was dissolved in 3 ml of NMP, admixed with sodium hydride (55% in oil) (120 mg, 3 mmol) and, after addition of 3-chloro-6-isopropoxypyridazine (259 mg, 1.5 mmol) stirred in a microwave reactor at 150° C. for 15 min. Following addition of ethyl acetate and water, the organic phase was separated off, concentrated and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 40mg (8%), M+H+: 344.2.

Workup

customthe organic phase was separated off
concentrationconcentrated
custompurified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record: ord-29f8be87b45d4bdb9e589d83e2752d15
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08470841B2

Reaction notes

Loading…