(2-Methoxyethyl)(methyl)amine → HCID 67314445, compound

HRID 1254109Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

Following the method described in Example 19, 5-fluoro-3-(2-vinyl-7H-furo[3,4-b]pyridin-5-ylidene)-1,3-dihydro-indol-2-one (65 mg, 0.22 mmol) and (2-methoxyethyl)methylamine (300 mg, 3.99 mmol) and AcOH (12 drops) are heated 100° C. for 2 h. Additional (2-methoxyethyl)methylamine is added and heating is continued for 1 hr. The reaction mixture is cooled and treated with triethylamine (10 drops). The reaction mixture is loaded onto silica gel and purified by chromatography (silica gel, MeOH-Chloroform). The product containing fractions are concentrated and the residue is triturated with EtOAc-hexane. The solid which formed is collected by filtration and dried under vacuum to provide the title compound (53 mg, 65%) as a yellow solid.

Workup

temperatureheating
temperatureThe reaction mixture is cooled
custompurified by chromatography (silica gel, MeOH-Chloroform)
additionThe product containing fractions
concentrationare concentrated
customthe residue is triturated with EtOAc-hexane
customThe solid which formed
filtrationis collected by filtration
customdried under vacuum

Sources & evidence

ORD record: ord-c549cea9290a4a46a50ac132daaa07ab
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455535B2

Reaction notes

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