Ethylenediamine → HCID 71254506, compound

HRID 540319Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([N:12]2[CH2:18][CH2:17][CH2:16][C:15]3[CH:19]=[CH:20][C:21]([O:23][CH2:24][CH3:25])=[CH:22][C:14]=3[CH2:13]2)[CH:3]=1.[CH2:26]([NH2:29])[CH2:27][NH2:28]>>[CH2:24]([O:23][C:21]1[CH:20]=[CH:19][C:15]2[CH2:16][CH2:17][CH2:18][N:12]([C:4]3[CH:3]=[C:2]([NH:28][CH2:27][CH2:26][NH2:29])[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[N:5]=3)[CH2:13][C:14]=2[CH:22]=1)[CH3:25]

Participants

Reactant 2

HCID 3301Ethylenediamine

HCID 71255473HCID 71255473, compound

Product 1

HCID 71254506HCID 71254506, compoundYield 40%

Conditions

Temperature: 160 °C

Procedure

The mixture of 2-(4-chloroquinolin-2-yl)-8-ethoxy-2,3,4,5-tetrahydro-1H-2-benzazepine (28 mg, 0.79 mmol) and ethane-1,2-diamine (0.5 mL) was heated with stirring in a 5 mL microwave process vial for 2 hours at 160° C. under microwave irradiation. The solvent was removed under reduced pressure and the residue was purified by preparative HPLC to give 12 mg of product (yield was 40%). MS obsd. (ESI+) [(M+H)+] 377. 1H NMR (400 MHz, CD3OD) δ ppm 7.88 (d, J=7.6 Hz, 1 H,), 7.62 (d, J=8.0 Hz, 1 H), 7.57 (m, 1 H), 7.51 (d, J=8.4 Hz, 1 H), 7.38 (m, 1 H), 7.19 (m, 2 H), 6.00 (s, 1 H), 4.78 (s, 2 H), 4.12 (m, 2 H), 3.99 (q, J=6.8 Hz, 2 H), 3.48 (m, 2 H), 2.98 (m, 4 H), 1.94 (m, 2 H), 1.34 (t, J=6.8 Hz, 3 H).

Workup

temperaturewas heated
customThe solvent was removed under reduced pressure
customthe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-d3e2b20d79384315a24f311c73b3625a
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871756B2

Reaction notes

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