Triphenylphosphine → HCID 16113323, compound

HRID 2240927Notes

Reaction equation

[NH2:1][C:2]1[N:3]([CH3:25])[C:4](=[O:24])[C:5]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH:21]([F:23])[F:22])=[CH:16][CH:15]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([OH:13])[CH:8]=2)[N:6]=1.[CH2:26](O)[CH2:27][CH:28]=[CH2:29].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[NH2:1][C:2]1[N:3]([CH3:25])[C:4](=[O:24])[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:29][CH2:28][CH:27]=[CH2:26])[CH:8]=2)([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH:21]([F:22])[F:23])=[CH:16][CH:15]=2)[N:6]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-amino-4-(4-(difluoromethoxy)phenyl)-4-(3-hydroxyphenyl)-1-methyl-1H-imidazol-5(4H)-one (0.070 g, 0.20 mmol), but-3-en-1-ol (0.023 g, 0.32 mmol), and PS—PPh3 (0.145 g, 0.32 mmol, 2.2 mmol/g) in THF (2 mL) is added diethylazodicarboxylate (0.058 g, 0.38 mmol) in THF (0.5 mL) dropwise. The mixture is stirred at 60° C. for 4 h. The solution is cooled to RT and the PPh3 is filtered and washed with CH2Cl2 and MeOH. The solvent is removed, the remaining material is absorbed onto Celite and purified by Flash Chromatography (15:1 CH2CL2:MeOH) to yield 2-amino-4-(3-(but-3-enyloxy)phenyl)-4-(4-(difluoromethoxy)phenyl)-1-methyl-1H-imidazol-5(4H)-one (0.051 g, 73%) as an off white foam.

Workup

temperatureThe solution is cooled to RT
filtrationthe PPh3 is filtered
washwashed with CH2Cl2 and MeOH
customThe solvent is removed
customthe remaining material is absorbed onto Celite
custompurified by Flash Chromatography (15:1 CH2CL2:MeOH)

Sources & evidence

ORD record: ord-92fd30dfb8624832be34a8346acd06c0
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723368B2

Reaction notes

Loading…