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

HRID 2190660

반응식

HRID 2190660 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7c51d01c96c04fc09b91fada97e578aa
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324385B2

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