1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(3-cyano-5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl)-2,2-diphenylacetamide

HRID 722717

Reaction equation

HRID 722717 reaction equation
CCN=C=NCCCN(C)C.[NH2:12][C:13]1[S:17][C:16]2[CH2:18][CH2:19][CH2:20][C:15]=2[C:14]=1[C:21]#[N:22].[C:23]1([CH:29]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36]C=2)[C:30]([OH:32])=O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[C:21]([C:14]1[C:15]2[CH2:20][CH2:19][CH2:18][C:16]=2[S:17][C:13]=1[NH:12][C:30](=[O:32])[CH:29]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:33]1[CH:34]=[CH:39][CH:38]=[CH:37][CH:36]=1)#[N:22]

Participants

4

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 187442,3-Diphenylpropionic acidHCID 2581822-amino-4H,5H,6H-cyclopenta(b)thiophene-3-carbonitrile

Product 1

HCID 1124364N-(3-cyano-5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl)-2,2-diphenylacetamideYield 23.9%

Procedure

EDCI (59 mg; 0.308 mmol) was added to a solution of 2-Amino-3-cyano-5,6-dihydro-4H-cyclopenta[b]thiophene (25 mg; 0.152 mmol) and 2,3-diphenylpropionic acid (70 mg; 0.309 mmol). After stirring for 19 h, the reaction mixture was applied directly to a silica gel column (Merck Silica gel 60; eluent: 10%–33% ethyl acetate/hexanes) to provide 13.0 mg (23%) of N-(3-Cyano-5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl)-2,2-diphenyl-acetamide as a white solid. EI-HRMS m/e calcd for C22H18N2OS (M+H+) 358.1140, found 358.1140.

Sources & evidence

ORD record
ord-f1f40e905e2c48af88cde6e83cdfe8cc
Source dataset
uspto-grants-2006_11
Patent number
US07138529B2

Linked notes

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