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

HRID 722714

反応式

HRID 722714 の反応式
[CH3:1][CH:2]([CH2:13][CH3:14])[CH:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:4](Cl)=[O:5].[NH2:15][C:16]1[S:20][C:19]2[CH2:21][CH2:22][CH2:23][C:18]=2[C:17]=1[C:24]#[N:25]>>[C:24]([C:17]1[C:18]2[CH2:23][CH2:22][CH2:21][C:19]=2[S:20][C:16]=1[NH:15][C:4](=[O:5])[CH:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH:2]([CH3:1])[CH2:13][CH3:14])#[N:25]

参加物

3

反応物 2

HCID 2581822-amino-4H,5H,6H-cyclopenta(b)thiophene-3-carbonitrileHCID 218860263-Methyl-2-phenylvaleryl chloride

生成物 1

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

実験手順

Reaction of 3-methyl-2-phenylvaleryl chloride (Prepared in Example 7, 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 which triturated with diethylether to give 94 mg of crude 3-Methyl-2-phenyl-pentanoic acid (3-cyano-5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl)-amide which was further purified by dissolving in methylene chloride and passing through a short plug of Merck Silica gel 60 to provide 82 mg (24%) of 3-Methyl-2-phenyl-pentanoic acid (3-cyano-5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl)-amide as a mixture of diastereomers. ES-HRMS m/e calcd for C26H38N2O2 (M+Ht) 411.3006, found 411.3011.

後処理

  1. customprovided after workup, crude which
  2. customtriturated with diethylether

出典と根拠

ORDレコード
ord-0b9368bdcff74ac98b7c4f8a337b30ef
出典データセット
uspto-grants-2006_11
特許番号
US07138529B2

関連ノート

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