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Ethyl Bromide → Tert-butyl{1-[4-(3-ethoxy-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]cyclobutyl}carbamate

HRID 2064457
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HRID 2064457 반응식
[OH:1][C:2]1[N:14]2[C:5]([C:6]3[CH:7]=[C:8]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:9]([C:15]4[CH:20]=[CH:19][C:18]([C:21]5([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:24][CH2:23][CH2:22]5)=[CH:17][CH:16]=4)=[N:10][C:11]=3[CH:12]=[CH:13]2)=[N:4][N:3]=1.Br[CH2:40][CH3:41]>[Ag]=O.CN1C(=O)CCC1>[CH2:40]([O:1][C:2]1[N:14]2[C:5]([C:6]3[CH:7]=[C:8]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[C:9]([C:15]4[CH:16]=[CH:17][C:18]([C:21]5([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:24][CH2:23][CH2:22]5)=[CH:19][CH:20]=4)=[N:10][C:11]=3[CH:12]=[CH:13]2)=[N:4][N:3]=1)[CH3:41]
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참가 물질

5

반응물 2

HCID 6332Ethyl BromideHCID 178452597HCID 178452597, 화합물

생성물 1

HCID 57805453Tert-butyl{1-[4-(3-ethoxy-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]cyclobutyl}carbamate

시약·촉매·용매 2

HCID 92152Silver(II) oxide촉매HCID 13387N-methyl-2-pyrrolidone용매

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온도
80 °C

실험 절차

To a microwave vial was added tert-butyl {1-[4-(3-hydroxy-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]cyclobutyl}carbamate (1-5e) (113 mg, 0.223 mmol), silver oxide (310 mg, 1.336 mmol), bromoethane (0.062 mL, 0.826 mmol), and finally NMP (1 mL). The reaction mixture was then heated to 80° C. under microwave irradiation for 10 minutes. Upon completion the reaction mixture was filtered and then purified by reverse phase column chromatography (Sunfire C18) eluting with 20 to 100% acetonitrile/(0.1% TFA/water) gradient. The appropriate fractions were then combined, suspended in ethyl acetate, washed with a saturated solution of sodium bicarbonate, water and brine, dried over sodium sulfate, filtered and concentrated in vacuo to give tert-butyl {1-[4-(3-ethoxy-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]cyclobutyl}carbamate (9-1) as a tan solid. MS (M+H)+: observed=536.4, calculated=536.64.

후처리

  1. filtrationUpon completion the reaction mixture was filtered
  2. custompurified by reverse phase column chromatography (Sunfire C18)
  3. washeluting with 20 to 100% acetonitrile/(0.1% TFA/water) gradient
  4. washwashed with a saturated solution of sodium bicarbonate, water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-51eed25c0bc646d48a103a6571492218
출처 데이터셋
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08288407B2

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