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Nitrogen → 6-(cyclopentyl)-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-One

HRID 897208
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HRID 897208 반응식
N#N.Br[C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][C:9](=[O:14])[CH:8]=[C:7]2[NH:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH:23]=[CH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:18][CH2:17]1.[Br-].[CH:32]1([Zn+])[CH2:36][CH2:35][CH2:34][CH2:33]1>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].[Cu]I>[CH:32]1([C:4]2[CH:5]=[C:6]3[C:11](=[CH:12][CH:13]=2)[O:10][C:9](=[O:14])[CH:8]=[C:7]3[NH:15][CH:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH:23]=[CH:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:18][CH2:17]2)[CH2:36][CH2:35][CH2:34][CH2:33]1
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참가 물질

7

반응물 3

HCID 947NitrogenHCID 737123526-Bromo-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-OneHCID 178419768HCID 178419768, 화합물

생성물 1

HCID 737123356-(cyclopentyl)-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-One수율 22.3%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
촉매
HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매
HCID 8028Tetrahydrofuran용매

반응 조건

온도
160 °C

실험 절차

Into a dry microwave vial under N2 was added 6-Bromo-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-one (20 mg, 0.046 mmol), Pd(dppf)Cl2 (about 5 mol %), and CuI (about 6 mol %) in dry THF (0.5 mL) followed by cyclopentyl zinc bromide (0.273 mL, 0.138 mmol (0.5M in THF)) dropwise. The solution was heated in the microwave for 10 minutes at 160° C., filtered, and was purified by Prep HPLC to give 4.4 mg (18%) of the desired compound as the TFA salt. MS (ESI(+)Q1MS m/z 429 (M+H)+; 1H NMR (300 MHz, MeOH) δ ppm. 1.62-2.13 (m, 10H), 2.40 (br d, 2H), 3.06-3.12 (m, 1H), 3.24(br t, 2H), 3.72 (br d, 2H), 3.96 (m, 3H), 5.42 (s, 1H), 6.31-6.40 (m, 1H), 6.96 (d, 1H), 7.23-7.54 (m. 8H), 7.90 (d, 1H).

후처리

  1. filtrationfiltered
  2. customwas purified by Prep HPLC

출처 및 근거

ORD 기록
ord-7d7324f61c1240b6b672dcdba24f86a0
출처 데이터셋
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06921821B2

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