Diethyl Ether → 4-(2-amino-3H-imidazol-4-yl)-2,3-dichloro-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]azepin-8-one

HRID 29790

반응식

HRID 29790 반응식
[Cl:1][C:2]1[NH:13][C:5]2[C:6](=[O:12])[NH:7][CH2:8][CH2:9][CH:10](O)[C:4]=2[C:3]=1[Cl:14].S(O)(O)(=O)=O.[NH2:20][C:21]1[NH:22][CH:23]=[CH:24][N:25]=1.CCOCC>CS(O)(=O)=O>[NH2:20][C:21]1[NH:25][C:24]([CH:10]2[CH2:9][CH2:8][NH:7][C:6](=[O:12])[C:5]3[NH:13][C:2]([Cl:1])=[C:3]([Cl:14])[C:4]2=3)=[CH:23][N:22]=1

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 135136Bis(2-amino-1H-imidazole) sulphateHCID 597892292,3-dichloro-4-hydroxy-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]azepin-8-one

생성물 1

HCID 597891934-(2-amino-3H-imidazol-4-yl)-2,3-dichloro-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]azepin-8-one

시약·촉매·용매 1

HCID 6395Methanesulfonic Acid용매

반응 조건

온도
45 °C

실험 절차

To a solution of 2,3-dichloro-4-hydroxy-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]azepin-8-one (60 mg, 0.256 mmol), prepared as in reference 2, in methanesulfonic acid (0.5 mL) is added 2-aminoimidazole sulfate (40.5 mg, 0.153 mmol). The mixture is stirred at 45° C. overnight, cooled to room temperature and Et2O (5 mL) is added resulting in brown oil. After discarding the supernatant, the oil is purified by silica gel column chromatography and eluted with MeOH—CH2Cl2 to give 4-(2-amino-3H-imidazol-4-yl)-2,3-dichloro-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]azepin-8-one; 1H NMR (Methanol-d4) δ 2.09-2.17 (m, 1H), 2.23-2.31 (m, 1H), 3.20-3.29 (m, 2H), 4.23 (t, 1H, J=3.6 Hz), 6.18 (s, 1H); m/z [M++1] 300.0.

후처리

  1. temperaturecooled to room temperature
  2. customresulting in brown oil
  3. customthe oil is purified by silica gel column chromatography
  4. washeluted with MeOH—CH2Cl2

출처 및 근거

ORD 기록
ord-0c3cf8259ecf4237833c40d66f62a5fb
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423031B2

연결된 노트

불러오는 중…