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 1064100Notes

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-2053f523b00b445d95c34aced5cf5df0
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06967198B2

Reaction notes

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