Tetrahydrofuran → 2-(3-Tert-butoxycarbonylamino pyridin-4-yl)-5-(trifluoromethyl)benzoxazole

HRID 884854

反応式

HRID 884854 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:28]=[N:27][CH:26]=[CH:25][C:10]=1[C:11]([NH:13][C:14]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:15]=1O)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].O1CCCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:28]=[N:27][CH:26]=[CH:25][C:10]=1[C:11]1[O:12][C:15]2[CH:16]=[CH:17][C:18]([C:20]([F:21])([F:23])[F:22])=[CH:19][C:14]=2[N:13]=1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 668802523-tert-butoxycarbonylamino-N-[2-hydroxy-5-(trifluoromethyl)phenyl]isonicotinamide

生成物 1

HCID 668794082-(3-Tert-butoxycarbonylamino pyridin-4-yl)-5-(trifluoromethyl)benzoxazole収率 40.6%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a mixture of 1.78 g of 3-tert-butoxycarbonylamino-N-[2-hydroxy-5-(trifluoromethyl)phenyl]isonicotinamide, 20 ml of tetrahydrofuran and 1.29 g of triphenylphosphine, 2.15 g of 40% toluene solution of diethyl azodicarboxylate was added dropwise at room temperature. The reaction mixture was stirred at room temperature for one hour and then stirred while heating at 50° C. for 30 minutes. The reaction mixture was cooled to room temperature, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.69 g of 2-(3-tert-butoxycarbonylamino pyridin-4-yl)-5-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 36”).

後処理

  1. additionwas added dropwise at room temperature
  2. stirringstirred
  3. temperaturewhile heating at 50° C. for 30 minutes
  4. temperatureThe reaction mixture was cooled to room temperature
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-77d02e1cb9e84237a02339ad7f7b896b
出典データセット
uspto-grants-2012_08
特許番号
US08242133B2

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