Benzenamine, 2-phenoxy- → HCID 9829962, compound

HRID 2305221Notes

Reaction equation

HRID 2305221 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C@@H:18]3[CH2:22][CH2:21][CH2:20][C@H:19]3[CH2:23][C:24]3[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=3)[C:27](O)=[O:28])[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:33]1[CH:38]=[CH:37][C:36]([O:39][C:40]2[C:45]([NH2:46])=[CH:44][CH:43]=[CH:42][CH:41]=2)=[CH:35][CH:34]=1.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C.CN(C)C1C=CN=CC=1.CCOC(C)=O>[O:39]([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][C:45]=1[NH:46][C:27](=[O:28])[C:26]1[CH:30]=[CH:31][CH:32]=[C:24]([CH2:23][C@@H:19]2[CH2:20][CH2:21][CH2:22][C@H:18]2[C:9]2[O:10][C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=2)[CH:25]=1)[C:36]1[CH:35]=[CH:34][CH:33]=[CH:38][CH:37]=1

Participants

7

Reactant 3

HCID 75899Benzenamine, 2-phenoxy-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11327698HCID 11327698, compound

Product 1

HCID 9829962HCID 9829962, compoundYield 51%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 3-{[(1S,2R)-2-(4,5-diphenyloxazol-2-yl)-1-cyclopentyl)methyl}benzoic acid (120 mg, 0.284 mmol) and 2-aminodiphenyl ether (68 ml, 0.369 mmol) in DMF (5 ml) was added 1-hydroxybenzotrioxazole (58 mg, 0.426 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (109 mg, 0.568 mmol), and 4-dimethylaminopyridine (27 mg, 0.284 mmol). After stirring the mixture at room temperature for 2 hours, the reaction mixture was heated at 80° C. for 3 hours. Then, the resultant mixture was diluted with EtOAc (30 ml), washed with 1N hydrochloric acid, water, saturated sodium hydrogencarbonate solution, water, and brine. The resultant mixture was dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane:EtOAc, 4:1 elution) to give N-(2-phenoxyphenyl)-3-{[(1S,2R)-2-(4,5-diphenyloxazol-2-yl)-1-cyclopentyl]methyl}benzamide (84.7 mg, 51%).

Workup

  1. temperaturethe reaction mixture was heated at 80° C. for 3 hours
  2. washwashed with 1N hydrochloric acid, water, saturated sodium hydrogencarbonate solution, water, and brine
  3. dry with materialThe resultant mixture was dried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography (hexane:EtOAc, 4:1 elution)

Sources & evidence

ORD record
ord-4066c3cb66fc47ba89f135183e4cf47e
Source dataset
uspto-grants-2002_08
Patent number
US06437146B1

Reaction notes

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