Trichloroacetyl chloride → 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-1H-imidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide

HRID 900254

반응식

HRID 900254 반응식
[Cl:1][C:2]1[S:6][C:5]([C:7]2[O:11][N:10]=[C:9]([CH2:12][N:13]3[CH:17]=[CH:16][N:15]=[CH:14]3)[CH:8]=2)=[CH:4][CH:3]=1.CCN(CC)CC.ClC(Cl)(Cl)[C:27](Cl)=[O:28].Cl.Cl.[CH:34]([N:37]1[CH2:42][CH2:41][CH:40]([NH2:43])[CH2:39][CH2:38]1)([CH3:36])[CH3:35]>C(Cl)Cl>[CH:34]([N:37]1[CH2:42][CH2:41][CH:40]([NH:43][C:27]([C:14]2[N:13]([CH2:12][C:9]3[CH:8]=[C:7]([C:5]4[S:6][C:2]([Cl:1])=[CH:3][CH:4]=4)[O:11][N:10]=3)[CH:17]=[CH:16][N:15]=2)=[O:28])[CH2:39][CH2:38]1)([CH3:36])[CH3:35]

참가 물질

6

반응물 4

HCID 6420Trichloroacetyl chlorideHCID 8471Triethylamine2회HCID 177503401-(Propan-2-yl)piperidin-4-amine dihydrochlorideHCID 691120685-(5-Chloro-thiophen-2-yl)-3-imidazol-1-ylmethyl-isoxazole

생성물 1

HCID 103881781-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-1H-imidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To a solution of 5-(5-Chloro-thiophen-2-yl)-3-imidazol-1-ylmethyl-isoxazole (85 mg) and NEt3 (89 μL) in DCM (3 mL) was added trichloroacetyl chloride (43 μL) dropwise at 0° C. The mixture was stirred for 5 min at 0° C. and for 30 min at RT. More NEt3 (133 μL) and 1-isopropyl-piperidin-4-ylamine dihydrochloride (88 mg) were added and stirring was continued for 2 h at RT. The mixture was concentrated and the residue was purified by preparative HPLC. The fractions containing the product were evaporated to provide 67 mg of the title compound as its trifluoroacetate salt. MS (ESI+): mi/e=434, chloro pattern.

후처리

  1. stirringstirring
  2. waitwas continued for 2 h at RT
  3. concentrationThe mixture was concentrated
  4. customthe residue was purified by preparative HPLC
  5. additionThe fractions containing the product
  6. customwere evaporated

출처 및 근거

ORD 기록
ord-855567cfc5f248899cc0bf9c88d2e0b3
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07358268B2

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