1,2-Dichloroethane → HCID 178450005、化合物

HRID 333426ノート

反応式

HRID 333426 の反応式
[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]

参加物

7

反応物 5

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

生成物 1

HCID 178450005HCID 178450005、化合物収率 22.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

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%.

後処理

  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)

出典と根拠

ORDレコード
ord-768b353424ab487e829cb0a3784ba18c
出典データセット
uspto-grants-2014_11
特許番号
US08877968B2

反応ノート

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