1,2-Dichloroethane → HCID 178450005, 화합물

HRID 333426노트

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HRID 333426 반응식
[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][NH:8][C:9](=[O:24])[NH:10][CH:11]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[C:12]([OH:14])=O)[N:3]=[CH:2]1.FC(F)(F)C(O)=O.[CH2:32]([O:36][C:37]1([CH:43]2[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]2)[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1)[CH2:33][CH2:34][CH3:35].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[CH2:32]([O:36][C:37]1([CH:43]2[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]2)[CH2:38][CH2:39][N:40]([C:12](=[O:14])[CH:11]([NH:10][C:9]([NH:8][CH2:7][CH2:6][C:4]2[N:3]=[CH:2][NH:1][CH:5]=2)=[O:24])[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH2:41][CH2:42]1)[CH2:33][CH2:34][CH3:35]

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 311Citric AcidHCID 757711-HydroxybenzotriazoleHCID 669879764-Butoxy-4-cyclohexylpiperidine trifluoroacetateHCID 178490381HCID 178490381, 화합물

생성물 1

HCID 178450005HCID 178450005, 화합물수율 22.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To 69 mg (0.21 mmol) of 2-{3-[2-(1H-imidazol-4-yl)ethyl]ureido}-3-(4-methoxyphenyl)-propanoic acid (cf. preparation 2-3) dissolved in 2 mL of DMF is added a solution of 71 mg (0.20 mmol) of 4-butoxy-4-cyclohexylpiperidine trifluoroacetate in 1.5 mL of DMF, 44 mg (0.23 mmol) of EDC and 33 mg (0.24 mmol) of HOBt. After 2 hours 30 minutes, the reaction medium is hydrolysed with aqueous 2% citric acid solution and then extracted with dichloromethane. The organic phase is then washed with aqueous 1N sodium hydroxide solution. The organic phase is dried over MgSO4, filtered and concentrated. This oil is chromatographed on silica gel (eluent: 8/2 DCM/MeOH). 25 mg of 1-[2-(4-butoxy-4-cyclohexylpiperidin-1-yl)-1-(4-methoxy-benzyl)-2-oxoethyl]-3-[2-(1H-imidazol-4-yl)ethyl]urea are obtained in a yield of 22%.

후처리

  1. extractionextracted with dichloromethane
  2. washThe organic phase is then washed with aqueous 1N sodium hydroxide solution
  3. dry with materialThe organic phase is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThis oil is chromatographed on silica gel (eluent: 8/2 DCM/MeOH)

출처 및 근거

ORD 기록
ord-768b353424ab487e829cb0a3784ba18c
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877968B2

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