Triethylamine → {1-[4-(4-Fluoro-phenyl)phthalazin-1-yl]piperidin-4-yl}-methyl-carbamic acid tert-butyl ester

HRID 1012960

반응식

HRID 1012960 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[N:4][N:3]=1.[C:19]([O:23][C:24](=[O:33])[N:25]([CH3:32])[CH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)([CH3:22])([CH3:21])[CH3:20].C(N(CC)CC)C>CN(C=O)C.ClCCl>[C:19]([O:23][C:24](=[O:33])[N:25]([CH:26]1[CH2:27][CH2:28][N:29]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)=[N:4][N:3]=2)[CH2:30][CH2:31]1)[CH3:32])([CH3:22])([CH3:20])[CH3:21]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 21152391-Chloro-4-(4-fluorophenyl)phthalazineHCID 27568064-N-Boc-4-N-Methyl-aminopiperidine

생성물 1

HCID 58157128{1-[4-(4-Fluoro-phenyl)phthalazin-1-yl]piperidin-4-yl}-methyl-carbamic acid tert-butyl ester수율 88%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

반응 조건

온도
130 °C

실험 절차

Add 1-chloro-4-(4-fluorophenyl)-phthalazine (3.00 g, 11.6 mmol) to a solution of methyl-piperidin-4-yl-carbamic acid tert-butyl ester (2.98 g, 13.9 mmol) and triethylamine (3.52 g., 34.8 mmol) in DMF (30 mL). Heat at 130° C. for 3 days. Dissolve the reaction mixture in dichloromethane and wash with brine. Dry the organic phase with sodium sulfate, filter, and concentrate under reduced pressure. Purify the resulting residue by flash chromatography (20:5:1, hexane:ethyl acetate: 2 M ammonia in methanol) to yield the title compound as a solid (4.45 g, 88%). ES/MS m/z 437.2 (M+1).

후처리

  1. washwash with brine
  2. dry with materialDry the organic phase with sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate under reduced pressure
  5. customPurify the resulting residue by flash chromatography (20:5:1, hexane:ethyl acetate: 2 M ammonia in methanol)

출처 및 근거

ORD 기록
ord-5c9f3cc8906441889ca44d7048524c4d
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981892B2

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