1,8-Diazabicyclo(5.4.0)undec-7-ene → [1-(4-Cyanonaphthalen-1-yl)piperidin-3-ylmethyl]carbamic acid tert-butyl ester

HRID 916361노트

반응식

HRID 916361 반응식
[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](F)=[CH:5][CH:4]=1)#[N:2].[NH:14]1[CH2:19][CH2:18][CH2:17][CH:16]([CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:15]1.C1CCN2C(=NCCC2)CC1>N1C=CC=CC=1>[C:24]([O:23][C:22](=[O:28])[NH:21][CH2:20][CH:16]1[CH2:17][CH2:18][CH2:19][N:14]([C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH2:15]1)([CH3:27])([CH3:25])[CH3:26]

참가 물질

5

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27367341-Cyano-4-fluoronaphthaleneHCID 2756030tert-butyl N-[(piperidin-3-yl)methyl]carbamate

생성물 1

HCID 69224037[1-(4-Cyanonaphthalen-1-yl)piperidin-3-ylmethyl]carbamic acid tert-butyl ester수율 71.1%

시약·촉매·용매 1

HCID 1049Pyridine용매

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온도
60 °C

실험 절차

1-Cyano-4-fluoronaphthalene (273 mg, 1.60 mmol), tert-butyl (piperidin-3-ylmethyl)carbamate (411 mg, 1.92 mmol) and DBU (25 μl, 0.16 mmol) were dissolved in pyridine (4 mL) and stirred at 60° C. for 4 days. The reaction was worked up in the same way as for 198RL60 followed by purification using silica gel column chromatography eluted with a stepwise gradient of 0-70% ethyl acetate in n-heptane, giving the desired compound (416 mg, 71%) as a white solid.

후처리

  1. customfollowed by purification
  2. washeluted with a stepwise gradient of 0-70% ethyl acetate in n-heptane

출처 및 근거

ORD 기록
ord-b200cc29be814ade8c3414993330c44d
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07268232B2

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