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Water → Methyl 2-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-6-chloroisonicotinate

HRID 2233822
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HRID 2233822 반응식
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.[Cl:15][C:16]1[CH:17]=[C:18]([CH:23]=[C:24](Cl)[N:25]=1)[C:19]([O:21][CH3:22])=[O:20].O.[Na+].[Cl-]>CN1C(=O)CCC1.CCOC(C)=O>[C:10]([O:9][C:8]([NH:7][CH:4]1[CH2:3][CH2:2][N:1]([C:24]2[CH:23]=[C:18]([CH:17]=[C:16]([Cl:15])[N:25]=2)[C:19]([O:21][CH3:22])=[O:20])[CH2:6][CH2:5]1)=[O:14])([CH3:11])([CH3:13])[CH3:12]
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참가 물질

7

반응물 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 93237Methyl 2,6-dichloroisonicotinate2회HCID 7238334-(N-Boc-amino)piperidine

생성물 1

HCID 86608242Methyl 2-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-6-chloroisonicotinate

시약·촉매·용매 2

HCID 8857
Ethyl Acetate
용매
HCID 13387N-methyl-2-pyrrolidone용매

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온도
150 °C

실험 절차

tert-Butyl piperidin-4-ylcarbamate (972 mg, 4.85 mmol), was dissolved in anhydrous NMP (5 ml). Methyl 2,6-dichloroisonicotinate (Intermediate 24, 1 g, 4.85 mmol) was added followed by TEA (675 μl, 4.85 mmol). The mixture was heated under microwave conditions at 150° C. for 10 minutes. Water (50 ml) and EtOAc (100 ml) were added, the aqueous phase was treated with solid NaCl and extracted with EtOAc (4×100 ml). The EtOAc layer was dried, concentrated in vacuo and purified by flash chromatography eluting with hexane:EtOAc (4:1) to give the title product as an off-white solid. (1.4 g).

후처리

  1. extractionextracted with EtOAc (4×100 ml)
  2. dry with materialThe EtOAc layer was dried
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography
  5. washeluting with hexane:EtOAc (4:1)

출처 및 근거

ORD 기록
ord-0a67e466361e4db2977a5287212d5a6e
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07709503B2

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