2-amino-4H,5H,6H-cyclopenta(b)thiophene-3-carbonitrile → N-(3-Cyano-5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl)-2-cyclopentyl-2-phenyl-acetamide

HRID 722716

Reaktionsgleichung

Reaktionsgleichung von HRID 722716
[C:1]([C:3]1[C:4]2[CH2:24][CH2:23][CH2:22][C:5]=2[S:6][C:7]=1[NH:8][C:9](=[O:21])[CH:10]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:11]([CH3:14])[CH2:12][CH3:13])#[N:2].N[C:26]1SC2CCCC=2C=1C#N>>[C:1]([C:3]1[C:4]2[CH2:24][CH2:23][CH2:22][C:5]=2[S:6][C:7]=1[NH:8][C:9](=[O:21])[CH:10]([CH:11]1[CH2:14][CH2:26][CH2:13][CH2:12]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)#[N:2]

Komponenten

3

Edukt 2

HCID 2581822-amino-4H,5H,6H-cyclopenta(b)thiophene-3-carbonitrileHCID 113936033-Methyl-2-phenyl-pentanoic acid (3-cyano-5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl)-amide

Produkt 1

HCID 11337065N-(3-Cyano-5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl)-2-cyclopentyl-2-phenyl-acetamide

Versuchsvorschrift

Reaction of α-phenylcyclopentaneacetyl chloride (Prepared in Example 12, Step1) and 2-Amino-3-cyano-5,6-dihydro-4H-cyclopenta[b]thiophene (164 mg; 1.0 mmol) according to the procedure outlined in Example 5 for 20 h at room temperature provided after workup, crude product which triturated with diethylether to give 111 mg of which was further purified by recrystallization from ethylacetate/hexanes to provide 44 mg (%) of N-(3-Cyano-5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl)-2-cyclopentyl-2-phenyl-acetamide as a light brown solid. EI-HRMS m/e calcd for C21H32N2OS (M+) 350.1453, found 350.1456.

Aufarbeitung

  1. customprovided after workup, crude product which
  2. customtriturated with diethylether
  3. customto give 111 mg of which
  4. customwas further purified by recrystallization from ethylacetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-58f7537ec8664bd79409308a1064b1be
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07138529B2

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