Tetrahydrofuran → Pyrido-[3,4-f][1,4]-diazepin-3-yl cyclopropyl carbinol

HRID 6217

反応式

HRID 6217 の反応式
C1([Mg]Br)CC1.[Mg].C1(Br)CC1.C[N:12]1[C:18](=O)[C:17]2[CH:20]=[N:21][CH:22]=[CH:23][C:16]=2[N:15]2C=NC(C=O)=[C:14]2[CH2:13]1.[O:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1>CN(C)P(N(C)C)(N(C)C)=O>[NH:15]1[C:16]2[CH:23]=[CH:22][N:21]=[CH:20][C:17]=2[CH:18]=[N:12][C:13]([CH:33]([CH:32]2[CH2:30][CH2:31]2)[OH:29])=[CH:14]1

参加物

7

反応物 5

HCID 8028Tetrahydrofuran3 回HCID 78037BromocyclopropaneHCID 5462224MagnesiumHCID 536871715,6-dihydro-5-methyl-6-oxo-4H-imidazo [1,5-a]-pyrido [3,4-f][1,4]-diazepine-3-carboxaldehydeHCID 178418630HCID 178418630、化合物

生成物 1

HCID 137226500Pyrido-[3,4-f][1,4]-diazepin-3-yl cyclopropyl carbinol

試薬・触媒・溶媒 1

HCID 12679Hexamethylphosphoramide溶媒

実験手順

To a solution of cyclopropyl magnesium bromide in dry tetrahydrofuran (prepared from 72 mg (3 mmole)) of magnesium and 362 mg (3 mmole) of cyclopropyl bromide in 4 ml of tetrahydrofuran was added at room temperature in one portion a suspension of 240 mg (1 mmole)of 5,6-dihydro-5-methyl-6-oxo-4H-imidazo [1,5-a]-pyrido [3,4-f][1,4]-diazepine-3-carboxaldehyde suspended in a mixture of 1 ml of tetrahydrofuran and 1 ml of hexamethyl-phosphoramide. After 1 hour, the reaction was quenched with aqueous ammonium chloride and extracted with dichloromethane. Column chromatography (SiO2 -5% methanol in dichloromethane) yielded 120 mg of 5,6-dihydro-5-methyl-6-oxo-4H-imidazo-1,5-a]-pyrido-[3,4-f][1,4]-diazepin-3-yl cyclopropyl carbinol as an oil, (43%).

後処理

  1. customthe reaction was quenched with aqueous ammonium chloride
  2. extractionextracted with dichloromethane

出典と根拠

ORDレコード
ord-5d6c2380db7048b1ba438d1bba8589f6
出典データセット
uspto-grants-1993_09
特許番号
US05247079

関連ノート

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