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 2175195ノート

反応式

HRID 2175195 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-69c5ff9435a94d8b9460d3c86ddeb614
出典データセット
uspto-grants-2015_06
特許番号
US09062056B2

反応ノート

読み込み中…