Hydrochloric Acid → N-(4-(3-Benzylpyrazin-2-yloxy)phenyl)pyridin-2-amine

HRID 473638노트

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HRID 473638 반응식
Cl[C:2]1[C:3]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][N:7]=1.[Br-].[CH2:23]([Zn+])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C1COCC1.Cl>>[CH2:23]([C:2]1[C:3]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][N:7]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

참가 물질

5

반응물 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 53485989N-(4-(3-chloropyrazin-2-yloxy)phenyl)pyridin-2-amineHCID 178419772HCID 178419772, 화합물

생성물 1

HCID 59374294N-(4-(3-Benzylpyrazin-2-yloxy)phenyl)pyridin-2-amine

반응 조건

온도
70 °C

실험 절차

A suspension of N-(4-(3-chloropyrazin-2-yloxy)phenyl)pyridin-2-amine (200 mg, 0.670 mmol), benzylzinc bromide, 0.5M in THF (6.7 mL, 3.35 mmol), and bis(di-t-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (80 mg, 0.11 mmol) was sparged with argon for 5 minutes then heated to 70° C. for 2 h. The reaction was then partitioned between EtOAc (30 mL) and sat NH4Cl (10 mL). The separated organic layer was dried over MgSO4, concentrated under reduced pressure, then purified on silica (40 g) eluting with 1.5-2.0% MeOH/DCM. The resulting residue was then dissolved in MeOH (5 mL) and 0.105 mL of HCl (5 M; 0.105 mL, 0.525 mmol) added. The resulting solid was isolated by filtration to give the title compound. MS (ESI positive ion) m/z: 355.1 (M+1). IC50 (uM) 0.250.

후처리

  1. customThe reaction was then partitioned between EtOAc (30 mL)
  2. dry with materialThe separated organic layer was dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. custompurified on silica (40 g)
  5. washeluting with 1.5-2.0% MeOH/DCM
  6. dissolutionThe resulting residue was then dissolved in MeOH (5 mL)
  7. customThe resulting solid was isolated by filtration

출처 및 근거

ORD 기록
ord-adeed2dc030f40139f78929909584496
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637500B2

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