Water → HCID 53303430, compound

HRID 871847Notes

Reaction equation

[NH2:1][C:2]1[N:12]([CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[C:6]2[N:7]=[C:8](Cl)[N:9]=[CH:10][C:5]=2[C:4](=[O:18])[C:3]=1[C:19]([NH2:21])=[O:20].[NH2:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[CH:25][CH:24]=1.O.C([O-])(O)=O.[Na+]>CN1C(=O)CCC1>[NH2:1][C:2]1[N:12]([CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[C:6]2[N:7]=[C:8]([NH:22][C:23]3[CH:24]=[CH:25][C:26]([N:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)=[CH:27][CH:28]=3)[N:9]=[CH:10][C:5]=2[C:4](=[O:18])[C:3]=1[C:19]([NH2:21])=[O:20]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 184 mg (0.60 mmol) of the product prepared in step 3.3 and 0.266 g (1.49 mmol) of N-(4-aminophenyl)morpholine (Lancaster) in 6 mL of NMP is placed in a 10 mL microwave tube. The sealed tube is placed in the microwave oven (CEM machine, Discover model) and the mixture is heated under pressure at 90°C. for 1 hour at a power of 100 W and then cooled to room temperature. 20 mL of water and then 5 mL of saturated aqueous NaHCO3 are added and the precipitate formed is drained by suction and dried in an oven. The crude solid is purified by chromatography on a column of silica, eluting with a dichloromethane/methanol gradient (98/2 to 95/5). 0.065 g of the expected product is obtained in the form of a beige-coloured powder. Yield=24%. m.p.=265°C. M+H+=450.

Workup

customis placed in a 10 mL microwave tube
temperaturecooled to room temperature
customthe precipitate formed
customdried in an oven
customThe crude solid is purified by chromatography on a column of silica
washeluting with a dichloromethane/methanol gradient (98/2 to 95/5)

Sources & evidence

ORD record: ord-d285606b25854484a07a936e9ba3d351
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975250B2

Reaction notes

Loading…