1,1'-Carbonyldiimidazole → (R)-3-(5-Cyano-2-oxo-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl)-3-phenyl-propionic acid ethyl ester

HRID 2175195노트

반응식

HRID 2175195 반응식
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C@@H:6]([NH:13][C:14]1[C:19]([NH2:20])=[CH:18][CH:17]=[C:16]([C:21]#[N:22])[N:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].C1N=CN([C:29](N2C=NC=C2)=[O:30])C=1.C1CCN2C(=NCCC2)CC1>C1COCC1>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C@@H:6]([N:13]1[C:14]2=[N:15][C:16]([C:21]#[N:22])=[CH:17][CH:18]=[C:19]2[NH:20][C:29]1=[O:30])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH3:2]

참가 물질

5

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 58497449(R)-3-(3-Amino-6-cyano-pyridin-2-ylamino)-3-phenyl-propionic acid ethyl ester

생성물 1

HCID 58497426(R)-3-(5-Cyano-2-oxo-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl)-3-phenyl-propionic acid ethyl ester수율 19%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of (R)-3-(3-amino-6-cyano-pyridin-2-ylamino)-3-phenyl-propionic acid ethyl ester (600 mg, 1.93 mmol) in THF (20 ml) was added CDI (630 mg, 3.87 mmol) and DBU (0.12 ml, 0.77 mmol). The resulting solution was stirred at room temperature for 18 hours after which time the reaction appeared complete. Added silica gel and concentrated. The remaining solid was purified via silica gel flash column chromatography (Companion, 12 g silica gel, 30-60% EtOAc/hexanes) to give 120 mg (19%) of the title compound.

후처리

  1. concentrationAdded silica gel and concentrated
  2. customThe remaining solid was purified via silica gel flash column chromatography (Companion, 12 g silica gel, 30-60% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-69c5ff9435a94d8b9460d3c86ddeb614
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062056B2

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