Ethylenediamine → HCID 71255375, compound

HRID 540307Notes

Reaction equation

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

Participants

Reactant 2

HCID 3301Ethylenediamine

HCID 71255395HCID 71255395, compound

Product 1

HCID 71255375HCID 71255375, compoundYield 18%

Conditions

Temperature: 160 °C

Procedure

The mixture of 7-bromo-2-(4,6-dichloroquinolin-2-yl)-2,3,4,5-tetrahydro-1H-2-benzazepine (200 mg, 0.47 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 38 mg of product (yield was 18%). MS obsd. (ESI+) [(M+H)+] 445, 1H NMR (400 MHz, CD3OD) δ ppm 7.90 (d, J=2.4 Hz, 1 H), 7.49 (d, J=8.8 Hz, 1 H), 7.41 (m, 1 H), 7.35 (m, 1 H), 7.31 (m, 2 H), 5.99 (s, 1 H), 4.80 (s, 2 H), 4.13 (m, 2 H), 3.40 (m, 2 H), 3.00 (m, 4 H), 1.90 (m, 2 H).

Workup

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

Sources & evidence

ORD record: ord-1daf5bdd97674f3b900d1d7b89b50e72
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871756B2

Reaction notes

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