1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 59404401, compound

HRID 1873670Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][C:18]([N:20]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:21][C:22]([C:24]2[C:34]3=[C:35]4[C:30](=[CH:31][CH:32]=[CH:33]3)[CH2:29][CH2:28][CH2:27][N:26]4[CH:25]=2)=O)=[O:19])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1CCN2C(=NCCC2)CC1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[C:18](=[O:19])[N:20]([C:36]([O:38][C:39]([CH3:40])([CH3:41])[CH3:42])=[O:37])[CH2:21][C:22]=2[C:24]2[C:34]3=[C:35]4[C:30](=[CH:31][CH:32]=[CH:33]3)[CH2:29][CH2:28][CH2:27][N:26]4[CH:25]=2)=[CH:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 3-(2-{tert-butoxycarbonyl-[2-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-2-oxo-ethyl]-amino}-2-oxo-ethyl)-indole-1-carboxylic acid tert-butyl ester (1.04 g, 1.82 mmol) and DBU (0.27 mL, 1.91 mmol) in anhydrous DMF (20 mL) was stirred at 110° C. for 2 h. The mixture was cooled and evaporated. The residue was purified by silica gel column chromatography (eluent: 4/1 then 3/1 hexane/EtOAc) to give 3-[1-tert-butoxycarbonyl-4-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-2-oxo-2,5-dihydro-1H-pyrrol-3-yl]-indole-1-carboxylic acid tert-butyl ester as a yellow foamy solid (0.64 g, 64%). 1H NMR (400 MHz, DMSO-d6) δ: 8.13 (d, J=8.8 Hz, 1H), 7.72 (s, 1H), 7.47 (s, 1H), 7.30 (m, 1H), 7.05 (m, 3H), 6.89 (m, 2H), 5.00 (s, 2H), 4.03 (t, J=5.6 Hz, 2H), 2.88 (t, J=5.6 Hz, 2H), 2.03 (m, 2H), 1.65 (s, 9H), 1.54 (s, 9H). LCMS: m/e 554.21 [M+H].

Workup

temperatureThe mixture was cooled
customevaporated
customThe residue was purified by silica gel column chromatography (eluent

Sources & evidence

ORD record: ord-2fb245f17f054008aa294e12d8ce4d68
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304425B2

Reaction notes

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