Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → 2-{[4-(Dimethylaminomethyl)piperidin-1-yl]carbonylamino}-4-(4-{3-[2-(4-fluorophenyl)acetyl]thioureido}phenoxy)pyridine

HRID 492884노트

반응식

HRID 492884 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([N:11]=[C:12]=[S:13])=[O:10])=[CH:4][CH:3]=1.[NH2:14][C:15]1[CH:40]=[CH:39][C:18]([O:19][C:20]2[CH:25]=[CH:24][N:23]=[C:22]([NH:26][C:27]([N:29]3[CH2:34][CH2:33][CH:32]([CH2:35][N:36]([CH3:38])[CH3:37])[CH2:31][CH2:30]3)=[O:28])[CH:21]=2)=[CH:17][CH:16]=1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C1(C)C=CC=CC=1.C(O)C>[CH3:38][N:36]([CH2:35][CH:32]1[CH2:31][CH2:30][N:29]([C:27]([NH:26][C:22]2[CH:21]=[C:20]([O:19][C:18]3[CH:17]=[CH:16][C:15]([NH:14][C:12]([NH:11][C:9](=[O:10])[CH2:8][C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)=[S:13])=[CH:40][CH:39]=3)[CH:25]=[CH:24][N:23]=2)=[O:28])[CH2:34][CH2:33]1)[CH3:37]

참가 물질

6

반응물 3

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 231532482-(4-Fluorophenyl)acetyl isothiocyanateHCID 231533224-(4-Aminophenoxy)-2-{[4-(dimethylaminomethyl)piperidin-1-yl]carbonylamino}pyridine

생성물 1

HCID 576775602-{[4-(Dimethylaminomethyl)piperidin-1-yl]carbonylamino}-4-(4-{3-[2-(4-fluorophenyl)acetyl]thioureido}phenoxy)pyridine수율 30%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 1140Toluene용매

실험 절차

After adding a solution of 2-(4-fluorophenyl)acetyl isothiocyanate in toluene (0.2 M, 3.0 ml) to a solution of 4-(4-aminophenoxy)-2-{[4-(dimethylaminomethyl)piperidin-1-yl]carbonylamino}pyridine (79 mg) and (+)-10-camphorsulfonic acid (49.7 mg) in ethanol (3.0 ml) at room temperature, the mixture was stirred overnight. The reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate. The organic layer was washed with saturated aqueous sodium hydrogencarbonate and brine in that order and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (Fuji Silysia NH, eluent; ethyl acetate:heptane=4:1) to provide the title compound (36.5 mg, 30%) as white powder.

후처리

  1. customThe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate
  2. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate and brine in that order
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was purified by silica gel column chromatography (Fuji Silysia NH, eluent; ethyl acetate:heptane=4:1)

출처 및 근거

ORD 기록
ord-ed3fc9fc776841eeb294bc4fa78cdb11
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531532B2

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