Toluene → HCID 90023045, compound

HRID 56293Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([NH:14][C:15](=[O:20])[CH2:16][C:17](=O)[CH3:18])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.[C:21]([C:23]1[CH:24]=[C:25]([CH:31]=[CH:32][CH:33]=1)[O:26][CH2:27][C:28]([NH2:30])=O)#[CH:22].C1(C)C=CC=CC=1.[NH4+].[Cl-]>C1(C)C(C)=CC=CC=1.C([O-])(C)C.C([O-])(C)C.C([O-])(C)C.C([O-])(C)C.[Ti+4]>[Cl:1][C:2]1[CH:3]=[C:4]([N:14]2[C:15](=[O:20])[CH:16]=[C:17]([CH3:18])[N:30]=[C:28]2[CH2:27][O:26][C:25]2[CH:31]=[CH:32][CH:33]=[C:23]([C:21]#[CH:22])[CH:24]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

Conditions

Temperature: 165 °C

Procedure

A mixture of N-(3-chloro-4-morpholinophenyl)-3-oxobutanamide (0.80 g, 2.85 mmol), 2-(3-ethynylphenoxy)acetamide (1.0 g, 5.71 mmol) and titanium tetraisopropanolate (6.76 mL) in xylene (20 mL) was stirred at 165° C. for 24 h. The mixture was cooled to rt and 50 mL of toluene and 60 mL of saturated NH4Cl aqueous solution were added. The resulting mixture was stirred at rt overnight and filtered and the filtrate was extracted with DCM (150 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as a yellow solid (0.60 g, 50%). The compound was characterized by the following spectroscopic data:

Workup

temperatureThe mixture was cooled to rt
stirringThe resulting mixture was stirred at rt overnight
filtrationfiltered
extractionthe filtrate was extracted with DCM (150 mL×3)
dry with materialThe combined organic layers were dried over anhydrous Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1)

Sources & evidence

ORD record: ord-f1ff9925b828427189b31f80a9d6b9ee
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434695B2

Reaction notes

Loading…