Morpholine → methyl 13-Cyclohexyl-6-(morpholinylcarbonyl)-5H-indolo[2,1-a][2]benzazepine-10-carboxylic acid

HRID 860715Notes

Reaction equation

[CH3:1]N(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH:23]1([C:29]2[C:30]3[CH:31]=[CH:32][C:33]([C:50]([O:52]C)=[O:51])=[CH:34][C:35]=3[N:36]3[CH:42]=[C:41]([C:43](O)=[O:44])[CH2:40][C:39]4[CH:46]=[CH:47][CH:48]=[CH:49][C:38]=4[C:37]=23)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.[NH:54]1[CH2:59][CH2:58][O:57][CH2:56][CH2:55]1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH3:1][C:49]1[C:38]2[C:37]3=[C:29]([CH:23]4[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]4)[C:30]4[CH:31]=[CH:32][C:33]([C:50]([OH:52])=[O:51])=[CH:34][C:35]=4[N:36]3[CH:42]=[C:41]([C:43]([N:54]3[CH2:59][CH2:58][O:57][CH2:56][CH2:55]3)=[O:44])[CH2:40][C:39]=2[CH:46]=[CH:47][CH:48]=1

Participants

Conditions

Temperature: 22 °C

Procedure

TBTU (145 mg, 0.45 mmol) was added to a stirred solution of 14a (R=H, 125 mg, 0.30 mmol), morpholine (26 μL, 0.30 mmol), and N,N-diisopropylethylamine 200 μL, 1.15 mmol) in DMF (2 mL). The mixture was stirred at 22° C. for 20 min. The resulting solution was injected on a Shimadzu preparative liquid chromatograph. The product containing fraction was concentrated on a Speed Vac® to leave methyl 13-Cyclohexyl-6-(morpholinylcarbonyl)-5H-indolo[2,1-a][2]benzazepine-10-carboxylic acid as a yellow solid (64 mg, 44%). ESI-MS m/z 487 (MH+), 1H NMR (500 MHz, CDCl3) δ 1.21 (m, 1 H), 1.34–1.55 (m, 3 H), 1.77 (m, 2 H), 1.91 (m, 1 H), 2.06 (m, 3 H), 2.83 (m, 1 H), 2.97–3.85 (m, 8 H), 3.97 (s, 3 H), 4.45 (m, 1 H), 5.07 (m, 1 H), 6.89 (s, 1 H), 7.41 (d, 1 H), 7.49 (m, 2 H), 7.57 (m, 1 H), 7.75 (m, 1 H), 7.89 (d, J=8.55 Hz, 1 H), 8.15 (s, 1 H).

Workup

additionThe product containing fraction
concentrationwas concentrated on a Speed Vac®

Sources & evidence

ORD record: ord-d46d017fca7543f29cde5256858d200c
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07153848B2

Reaction notes

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