Triethylamine → HCID 178524305, Verbindung

HRID 2053534Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2053534
Cl.[C:2]1([C@H:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:11][C:10]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[N:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:36]([O:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:37]>CN(C)C1C=CN=CC=1.ClCCl>[C:39]1([O:38][C:36]([N:9]2[C@H:8]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:11]=[C:10]2[NH:19][CH2:20][C:21]2[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=2)=[O:37])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 68568666(4S,5R)-N-[(4-fluorophenyl)methyl]-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-amine;hydrochloride

Produkt 1

HCID 178524305HCID 178524305, VerbindungAusbeute 82,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of (cis-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl)-(4-fluorobenzyl)amine (86) (100 mg, 0.26 mmol), triethylamine (0.091 mL, 0.656 mmol), 4-dimethylamino-pyridine (10 mg) in dichloromethane (10 mL) is added phenyl chloroformate (0.033 mL, 0.262 mmol), and the mixture is stirred at RT overnight. The reaction mixture is diluted with dichloromethane and washed with water, and the organic layer is dried (MgSO4), filtered, and evaporated. The residue is purified by chromatography on silica gel; gradient elution with heptane: EtOAc (70:30-60:40) gives 100 mg of the product 123. 1H NMR (CDCl3) δ 7.50-7.40 (m, 2H), 7.40-7.10 (m, 6H), 7.10-6.90 (m, 8H), 6.90-6.80 (m, 2H), 6.70-6.60 (m, 2H), 5.75-5.55 (m, 2H), 4.75-4.55 (m, 2H); MS: m/z 466 (M++1)

Aufarbeitung

  1. washwashed with water
  2. dry with materialthe organic layer is dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue is purified by chromatography on silica gel
  6. washgradient elution with heptane: EtOAc (70:30-60:40)

Quellen und Nachweise

ORD-Eintrag
ord-70418bdacfd14b5cbd8f4384c80aaddf
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07326792B2

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