N,N-Dimethylethylenediamine → N-(2-dimethylamino-ethyl)-2-(7-fluoro-1-oxo-1,3,4,10-tetrahydro-2H-azepino[3,4-b]indol-5-ylidene)-acetamide

HRID 29796Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]1[C:11](=[O:22])[NH:12][CH2:13][CH:14]=[C:15]([CH2:16][C:17]([N:19]=[N+]=[N-])=[O:18])[C:5]2=1.[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26]N>C1(C)C=CC=CC=1>[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26][NH:19][C:17](=[O:18])[CH:16]=[C:15]1[C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=3)[NH:7][C:6]=2[C:11](=[O:22])[NH:12][CH2:13][CH2:14]1

Participants

Conditions

Temperature: 110 °C

Procedure

A suspension of (7-Fluoro-1-oxo-1,2,3,10-tetrahydro-azepino[3,4-b]indol-5-yl)-acetyl azide, prepared as in reference 17, (10 mg, 0.33 mmol) and N,N-dimethylethylene-diamine (15 mg, 0.17 mmol) in dry toluene (1 mL) is heated at 110° C. for 1 hour. Toluene is removed in vacuum and the residue is purified by HPLC (C18 column, eluted with CH3CN/H2O with 0.5% TFA) to afford N-(2-dimethylamino-ethyl)-2-(7-fluoro-1-oxo-1,3,4,10-tetrahydro-2H-azepino[3,4-b]indol-5-ylidene)-acetamide; 1H NMR (DMSO-d6) δ 2.85 (s, 6H), 3.19-3.22 (m, 2H), 3.25-3.30 (m, 2H), 3.44-3.48 (m, 2H), 3.49 (q, 2H, J=6.8 Hz), 6.34 (s, 1H), 7.18 (dt, 1H, J1=2.8 Hz, J2=8.8 Hz), 7.50 (dd, 1H, J1=4.4 Hz, J2=8.8 Hz), 7.74 (dd, 1H, J1=2.8 Hz, J2=10.4 Hz), 8.39-8.44 (m, 2H), 9.36 (bs, 1H), 12.12 (s, 1H); m/z [M++1] 345.1.

Workup

customToluene is removed in vacuum
customthe residue is purified by HPLC (C18 column, eluted with CH3CN/H2O with 0.5% TFA)

Sources & evidence

ORD record: ord-444d699f6dbe4e46b2d0546ca48611c4
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07423031B2

Reaction notes

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