Tetrahydrofuran → HCID 117601306, compound

HRID 1773708Notes

Reaction equation

[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([NH2:27])[C:10]([NH:24][CH2:25][CH3:26])=[C:11]([C:13]3[C:22]([CH3:23])=[CH:21][CH:20]=[C:19]4[C:14]=3[CH:15]=[CH:16][CH:17]=[N:18]4)[CH:12]=2)=[C:5]([CH3:28])[O:4][N:3]=1.[C:29](N1C=CN=C1)(N1C=CN=C1)=[O:30].O1CCCC1>CCOC(C)=O>[CH3:1][C:2]1[C:6]([C:7]2[CH:12]=[C:11]([C:13]3[C:22]([CH3:23])=[CH:21][CH:20]=[C:19]4[C:14]=3[CH:15]=[CH:16][CH:17]=[N:18]4)[C:10]3[N:24]([CH2:25][CH3:26])[C:29](=[O:30])[NH:27][C:9]=3[CH:8]=2)=[C:5]([CH3:28])[O:4][N:3]=1

Participants

Conditions

Temperature: 105 °C

Procedure

4-(3,5-Dimethylisoxazol-4-yl)-N1-ethyl-6-(6-methylquinolin-5-yl)benzene-1,2-diamine (90 mg, 0.24 mmol) and 1,1′-carbonyldiimidazole (86.2 mg, 0.53 mmol) were added to tetrahydrofuran (10 ml) in a sealed vessel and heated to 105° C. overnight. The reaction mixture was the diluted in EtOAc and aqueous ammonium chloride and extracted with EtOAc (3 times). Organics were washed with ammonium chloride, water and brine and dried over sodium sulfate. Solvent was evaporated to dryness Crude material was purified by silica gel chromatography (DCM/MeOH as eluent) then by preparative HPLC to afford 5-(3,5-dimethylisoxazol-4-yl)-1-ethyl-7-(6-methylquinolin-5-yl)-1H-benzo[d]imidazol-2(3H)-one.

Workup

extractionaqueous ammonium chloride and extracted with EtOAc (3 times)
washOrganics were washed with ammonium chloride, water and brine
dry with materialdried over sodium sulfate
customSolvent was evaporated to dryness Crude material
customwas purified by silica gel chromatography (DCM/MeOH as eluent)

Sources & evidence

ORD record: ord-dc6790ba0f624bf8a26c9788e84e21a0
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255089B2

Reaction notes

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