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 2234774Notes

Reaction equation

[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

Participants

Conditions

Temperature: 45 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-16f5c31fcf9c4b3598cbddde852591dc
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07713958B2

Reaction notes

Loading…