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

HRID 890379

반응식

HRID 890379 반응식
[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]

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 142844-(Dimethylamino)pyridine촉매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-934662624998475283d244091759f70e
출처 데이터셋
uspto-grants-2006_02
특허 번호
US06995269B2

연결된 노트

불러오는 중…