Triethylamine → 1-(6-Oxo-2-phenyl-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)-pyrrolidine-2,5-dione

HRID 2375029Notes

Reaction equation

C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[O:32]=[C:33]1[C:44]2[C:45]3[C:37](=[C:38]([C:54]4[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=4)[NH:39][C:40]=3[CH:41]=[C:42]([NH:46][C:47](=[O:53])[CH2:48][CH2:49][C:50](O)=[O:51])[CH:43]=2)[CH:36]=[N:35][NH:34]1>CN(C)C=O>[O:32]=[C:33]1[C:44]2[C:45]3[C:37](=[C:38]([C:54]4[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=4)[NH:39][C:40]=3[CH:41]=[C:42]([N:46]3[C:50](=[O:51])[CH2:49][CH2:48][C:47]3=[O:53])[CH:43]=2)[CH:36]=[N:35][NH:34]1

Participants

Conditions

Temperature: 22 °C

Procedure

Triethylamine (0.18 mmol, 0.025 mL) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.04 mmol, 0.013 g) were added to a solution of the title compound of Example 8 (0.013 g, 0.036 mmol) in N,N-dimethylformamide (0.05 M, 0.75 mL). The reaction mixture was stirred at 22° C. for 12 hours and concentrated under reduced pressure. The yellow solid was triturated with methanol (3.0 mL), collected by filtration, and washed with methanol (4.0 mL) and diethyl ether (5.0 mL) to afford the title compound (5.8 mg) in 47% yield.

Workup

concentrationconcentrated under reduced pressure
customThe yellow solid was triturated with methanol (3.0 mL)
filtrationcollected by filtration
washwashed with methanol (4.0 mL) and diethyl ether (5.0 mL)

Sources & evidence

ORD record: ord-e9e5ccafcf154b7582d4586ff57e739a
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07462713B2

Reaction notes

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