1,2-Dichloroethane → (4-Azido-phenyl)-(7-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-methanone

HRID 890379

反応式

HRID 890379 の反応式
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11][C:5]=2[CH:4]=1.[N:14]([C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1C(O)=O)=[N+:15]=[N-:16].C(Cl)CCl.CCN(C(C)C)C(C)C.C1C[O:42][CH2:41]C1>CN(C1C=CN=CC=1)C>[N:14]([C:17]1[CH:18]=[CH:22][C:23]([C:41]([N:9]2[CH2:10][CH2:11][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:13]=[CH:12][C:6]=3[CH2:7][CH2:8]2)=[O:42])=[CH:24][CH:25]=1)=[N+:15]=[N-:16]

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 53255602-Azidobenzoic acidHCID 138533487-Methoxy-2,3,4,5-tetrahydro-1h-3-benzazepine

生成物 1

HCID 22250962(4-Azido-phenyl)-(7-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-methanone

試薬・触媒・溶媒 1

HCID 142844-(Dimethylamino)pyridine触媒

実験手順

7-Methoxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (1 equivalent) was dissolved in THF (0.1 M) along with azidobenzoic acid (1.5 equivalents), EDC (1.5 equivalents), DMAP (0.18 equivalents), and DIEA (1.5 equivalents). The reaction was stirred at room temperature overnight. The reaction was then washed with 10% citric acid, saturated sodium carbonate, and brine. The organic layer was then dried over sodium sulfate and the organic solvent removed under reduced pressure. The material was then purified via flash chromatography using 8% acetone/1% ammonia solution/petroleum spirit running solvent to give the title compound. (MH+) 323.2.

後処理

  1. washThe reaction was then washed with 10% citric acid, saturated sodium carbonate, and brine
  2. dry with materialThe organic layer was then dried over sodium sulfate
  3. customthe organic solvent removed under reduced pressure
  4. customThe material was then purified via flash chromatography

出典と根拠

ORDレコード
ord-934662624998475283d244091759f70e
出典データセット
uspto-grants-2006_02
特許番号
US06995269B2

関連ノート

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