1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-{4-[5-(3-Iodo-4-methyl-phenylcarbamoyl)-pyridin-2-yl]-piperazine-1-carbonyl}-cyclohexanecarboxylic acid

HRID 2190660

反応式

HRID 2190660 の反応式
[I:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:23])[C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[N:13][CH:12]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[C@H:24]1([C:33](O)=[O:34])[CH2:29][CH2:28][C@H:27]([C:30]([OH:32])=[O:31])[CH2:26][CH2:25]1.CCN=C=NCCCN(C)C>CN(C=O)C>[I:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:18][CH2:19][N:20]([C:33]([CH:24]4[CH2:25][CH2:26][CH:27]([C:30]([OH:32])=[O:31])[CH2:28][CH2:29]4)=[O:34])[CH2:21][CH2:22]3)=[N:13][CH:12]=2)=[O:23])[CH:5]=[CH:6][C:7]=1[CH3:8]

参加物

5

反応物 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 59318071N-(3-Iodo-4-methyl-phenyl)-6-piperazin-1-yl-nicotinamideHCID 178525731HCID 178525731、化合物

生成物 1

HCID 593179934-{4-[5-(3-Iodo-4-methyl-phenylcarbamoyl)-pyridin-2-yl]-piperazine-1-carbonyl}-cyclohexanecarboxylic acid収率 12.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of N-(3-iodo-4-methyl-phenyl)-6-piperazin-1-yl-nicotinamide (60 mg, 0.14 mmol), trans-1,4-cyclohexane dicarboxylic acid (122 mg, 0.71 mmol) in DMF (10 mL) was treated with EDCI (130 mg, 0.71 mmol). After stirring overnight the reaction mixture was partitioned between EtOAc and water. The water layer was made basic to pH 13 with solid NaOH. The EtOAc layer was removed and then the water layer was acidified to pH 5 with aq conc. HCl and extracted again with EtOAc. The EtOAc layer obtained after the latter extraction was dried over Na2SO4, filtered and concentrated to the product (10 mg, Yield: 12%). HRMS m/z calcd for C25H29N4O4I [M+H]+: 577.1306. Found: 577.1306.

後処理

  1. customwas partitioned between EtOAc and water
  2. customThe EtOAc layer was removed
  3. extractionextracted again with EtOAc
  4. customThe EtOAc layer obtained
  5. extractionafter the latter extraction
  6. dry with materialwas dried over Na2SO4
  7. filtrationfiltered

出典と根拠

ORDレコード
ord-7c51d01c96c04fc09b91fada97e578aa
出典データセット
uspto-grants-2012_12
特許番号
US08324385B2

関連ノート

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