2-Methyl-5-phenylfuran-3-carbonyl chloride → Methyl 2-[(4-{2-[(2-methyl-5-phenyl-3-furoyl)amino]ethyl)phenoxy)methyl]benzoate

HRID 2111984Notes

Reaction equation

HRID 2111984 reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][C:6]=1[C:7](Cl)=[O:8].Cl.[NH2:17][CH2:18][CH2:19][C:20]1[CH:37]=[CH:36][C:23]([O:24][CH2:25][C:26]2[CH:35]=[CH:34][CH:33]=[CH:32][C:27]=2[C:28]([O:30][CH3:31])=[O:29])=[CH:22][CH:21]=1>C(Cl)Cl>[CH3:1][C:2]1[O:3][C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][C:6]=1[C:7]([NH:17][CH2:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([O:24][CH2:25][C:26]2[CH:35]=[CH:34][CH:33]=[CH:32][C:27]=2[C:28]([O:30][CH3:31])=[O:29])=[CH:36][CH:37]=1)=[O:8]

Participants

4

Reactant 2

HCID 27764322-Methyl-5-phenylfuran-3-carbonyl chlorideHCID 68872919Methyl 2-{[4-(2-aminoethyl)phenoxy]methyl}benzoate hydrochloride

Product 1

HCID 68869789Methyl 2-[(4-{2-[(2-methyl-5-phenyl-3-furoyl)amino]ethyl)phenoxy)methyl]benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Methyl-5-phenylfuran-3-carbonyl chloride (36.4 mg, 0.165 mmol) and methyl 2-{[4-(2-aminoethyl)phenoxy]methyl}benzoate hydrochloride (53 mg, 0.165 mmol) were mixed in DCM (4 ml). PS-DIBA (3.66 mmol/g, 135 mg, 0.494 mmol) was added. The mixture was shaken at room temperature overnight. LC-MS showed there was only a trace amount of desired product and a big peak of 2-methyl-5-phenyl-3-furoic acid. TBTU (55 mg, 0.17 mmol) was added. The mixture was shaken for 2 hours and filtered. The filtrate was evaporated to dryness. Chromatography of the residue on a column (ISOLUTE® SI, 2 g/6 ml) using DCM and then MeOH/DCM (0.5:99.5) as eluant gave 34 mg the desired product, yield 44%.

Workup

  1. additionPS-DIBA (3.66 mmol/g, 135 mg, 0.494 mmol) was added

Sources & evidence

ORD record
ord-0548f73e55374d439e46b48bfcd6e751
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

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