N-(4-(3-(2,3-Dihydrofuran-2-YL)pyridin-2-yloxy)phenyl)pyridin-2-amine → N-(4-(3-(Tetrahydrofuran-2-YL)pyridin-2-yloxy)phenyl)pyridin-2-amine

HRID 473662노트

반응식

HRID 473662 반응식
[O:1]1[CH:5]=[CH:4][CH2:3][CH:2]1[C:6]1[C:7]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[CH:15][CH:14]=2)=[N:8][CH:9]=[CH:10][CH:11]=1>[Pd].C(O)C>[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]1[C:7]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[CH:15][CH:14]=2)=[N:8][CH:9]=[CH:10][CH:11]=1

참가 물질

4

반응물 1

HCID 59374334N-(4-(3-(2,3-Dihydrofuran-2-YL)pyridin-2-yloxy)phenyl)pyridin-2-amine

생성물 1

HCID 59374242N-(4-(3-(Tetrahydrofuran-2-YL)pyridin-2-yloxy)phenyl)pyridin-2-amine

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

To a 150 mL round bottom flask was added N-(4-(3-(2,3-dihydrofuran-2-yl)pyridin-2-yloxy)phenyl)pyridin-2-amine (660 mg, 1.992 mmol) and ethanol (7967 μL) before adding palladium, 10% wt. on activated carbon (70 mg, 0.658 mmol) portionwise. The flask was evacuated and backfilled with hydrogen under atmospheric pressure before allowing to stir at room temperature under hydrogen. The reaction was complete after 3 h. After dilution with ethyl acetate, the black suspension was filtered through a pad of Celite while rinsing with ethyl acetate (3×25 mL) before concentrating to a pale yellow residue. The residue was taken up in 5 mL DCM and applied directly to silica for purification (0 to 50% ethyl acetate/hexanes over 35 minutes). The target compound was isolated as a white solid. MS (ESI, pos. ion) m/z: 334.2 (M+1). IC50 (uM) 0.225.

후처리

  1. customThe flask was evacuated
  2. filtrationAfter dilution with ethyl acetate, the black suspension was filtered through a pad of Celite
  3. washwhile rinsing with ethyl acetate (3×25 mL)
  4. concentrationbefore concentrating to a pale yellow residue
  5. customapplied directly to silica for purification (0 to 50% ethyl acetate/hexanes over 35 minutes)
  6. customThe target compound was isolated as a white solid

출처 및 근거

ORD 기록
ord-e4d0120a7f3940919a6f00aaa8c9b35c
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637500B2

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